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Practical, Large-Scale Preparation of Ni(tmeda)(o-tol)Cl 实用、大规模制备 Ni(tmeda)(邻甲苯)Cl
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-11-15 DOI: 10.1021/acs.oprd.4c00408
Morgan E. John, Daven Foster, Stephen A. Moggach, George A. Koutsantonis, Reto Dorta, Scott G. Stewart
{"title":"Practical, Large-Scale Preparation of Ni(tmeda)(o-tol)Cl","authors":"Morgan E. John, Daven Foster, Stephen A. Moggach, George A. Koutsantonis, Reto Dorta, Scott G. Stewart","doi":"10.1021/acs.oprd.4c00408","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00408","url":null,"abstract":"A convenient, inexpensive synthesis of the previously reported, well-defined complex Ni(tmeda)(<i>o</i>-tol)Cl is described. This protocol enables rapid and safe access to Ni(tmeda)(<i>o</i>-tol)Cl, obviating the use of the hazardous reagent AlMe<sub>3</sub> or air-sensitive Ni(COD)<sub>2</sub>. Ni(tmeda)(<i>o</i>-tol)Cl is prepared at room temperature from commercially available and easily synthesized precursor Ni(acac)<sub>2</sub> and can be isolated at gram scale in air via simple filtration. We expect this simple method to be attractive to chemical industry and academia given the types of solvents, reaction temperature, and reagents used.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"1 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637776","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Practical and Efficient Approach to Scalable Synthesis of Rucaparib Rucaparib 可扩展合成的实用高效方法
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-11-15 DOI: 10.1021/acs.oprd.4c00366
Jinjae Park, Cheol-Hong Cheon
{"title":"Practical and Efficient Approach to Scalable Synthesis of Rucaparib","authors":"Jinjae Park, Cheol-Hong Cheon","doi":"10.1021/acs.oprd.4c00366","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00366","url":null,"abstract":"A scalable synthesis of rucaparib was developed from methyl 5-fluoro-2-methyl-3-nitrobenzoate and 4-cyanobenzaldehyde. Methyl 5-fluoro-2-methyl-3-nitrobenzoate was converted into a 2-aminocinnamonitrile derivative, which was subjected to the imino-Stetter reaction with 4-cyanobenzaldehyde to yield trisubstituted indole-3-acetonitrile. The reduction of both nitriles, followed by azepinone scaffold construction and selective monomethylation, completed the synthesis of rucaparib. This synthetic route features the use of inexpensive starting materials, scalability, and ease of purification through recrystallization.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"22 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142642615","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Chemical and Biochemical Approaches to an Enantiomerically Pure 3,4-Disubstituted Tetrahydrofuran Derivative at a Multikilogram Scale: The Power of KRED 以化学和生物化学方法制备千克级对映体纯度的 3,4-二取代四氢呋喃衍生物：KRED 的力量
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2024-11-14 DOI: 10.1021/acs.oprd.4c00388
Antony Bigot, Alain Rabion, Jean-Bernard Landier, Geoffrey Laronze, Frédéric Petit, Stéphanie Deprets, Jean-Marc Michot, Changxia Yuan, Fenglai Sun, Han Chen, Longlei Hou, Dalin Tang
{"title":"Chemical and Biochemical Approaches to an Enantiomerically Pure 3,4-Disubstituted Tetrahydrofuran Derivative at a Multikilogram Scale: The Power of KRED","authors":"Antony Bigot, Alain Rabion, Jean-Bernard Landier, Geoffrey Laronze, Frédéric Petit, Stéphanie Deprets, Jean-Marc Michot, Changxia Yuan, Fenglai Sun, Han Chen, Longlei Hou, Dalin Tang","doi":"10.1021/acs.oprd.4c00388","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00388","url":null,"abstract":"A scalable synthesis of (<i>3S,4S</i>)-4-methyltetrahydrofuran-3-ol involving a keto reductase-mediated enantio- and diastereoselective reduction of a racemic ketone substrate is reported. This chiral intermediate was initially produced using a low-yielding three-step synthesis from ketone, deemed not usable for future batches. Looking for a scalable and environmental process: an eco-design approach led to a one-step, highly enantio- and diastereoselective biocatalytic reduction of the ketone to the targeted intermediate (3<i>S</i>,4<i>S</i>)-4-methyltetrahydrofuran-3-ol. In addition, the reaction operates via dynamic kinetic resolution under unprecedented mild conditions of temperature and pH, allowing for a full conversion of the ketone substrate into the desired enantiomer. The new route led to a significant improvement of all the key performance indicators, including PMI, solvent, and waste.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"30 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142637775","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Optimized Synthesis of an Abemaciclib Intermediate: Improved Conditions for a Miyaura Borylation/Suzuki Coupling Process 优化合成 Abemaciclib 中间体：Miyaura Borylation/Suzuki Coupling 过程的改进条件
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2024-11-07 DOI: 10.1021/acs.oprd.4c0038110.1021/acs.oprd.4c00381
Michael P. Carroll*, Aobha Hickey, Ava Rogers, Cáoimhe J. Niland, Rachel A. O’Sullivan, Nachimuthu Muniraj, Kevin F. O’Sullivan, Patrick J. Guiry and Michael M. Murray, 
{"title":"Optimized Synthesis of an Abemaciclib Intermediate: Improved Conditions for a Miyaura Borylation/Suzuki Coupling Process","authors":"Michael P. Carroll*,&nbsp;Aobha Hickey,&nbsp;Ava Rogers,&nbsp;Cáoimhe J. Niland,&nbsp;Rachel A. O’Sullivan,&nbsp;Nachimuthu Muniraj,&nbsp;Kevin F. O’Sullivan,&nbsp;Patrick J. Guiry and Michael M. Murray,&nbsp;","doi":"10.1021/acs.oprd.4c0038110.1021/acs.oprd.4c00381","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00381https://doi.org/10.1021/acs.oprd.4c00381","url":null,"abstract":"<p >Improved reaction conditions have been developed for a telescoped Miyaura borylation/Suzuki coupling process, which is utilized in the synthesis of an abemaciclib intermediate. Key improvements include the in situ generation of a lipophilic base and tailored ligand selection for each palladium-catalyzed step. Optimizing ligand choice significantly reduced aryl scrambling, a major source of impurities in the borylation step. Additionally, the process improvements led to shortened reaction times and lower palladium loadings, resulting in a more efficient, higher-yielding process.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"28 11","pages":"4127–4136 4127–4136"},"PeriodicalIF":3.1,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640898","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Early Process Development of an LPAR1 Antagonist, GS-2278 LPAR1 拮抗剂 GS-2278 的早期工艺开发
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2024-11-05 DOI: 10.1021/acs.oprd.4c0036910.1021/acs.oprd.4c00369
Nathaniel Kadunce*, Anna M. Wagner*, Jeromy Cottell, Kathy Dao, Darryl D. Dixon, Blanka M. Hodur, Dane Holte, Michael A. Ischay, Jihun Kang, Seongtaek Kim, Young Ho Kim, Seung Moh Koo, Willard Lew, Lucas Man, Kashi Reddy Methuku, Henry Morrison, Patrick D. Parker, David A. Siler and Chloe Y. Wong, 
{"title":"Early Process Development of an LPAR1 Antagonist, GS-2278","authors":"Nathaniel Kadunce*,&nbsp;Anna M. Wagner*,&nbsp;Jeromy Cottell,&nbsp;Kathy Dao,&nbsp;Darryl D. Dixon,&nbsp;Blanka M. Hodur,&nbsp;Dane Holte,&nbsp;Michael A. Ischay,&nbsp;Jihun Kang,&nbsp;Seongtaek Kim,&nbsp;Young Ho Kim,&nbsp;Seung Moh Koo,&nbsp;Willard Lew,&nbsp;Lucas Man,&nbsp;Kashi Reddy Methuku,&nbsp;Henry Morrison,&nbsp;Patrick D. Parker,&nbsp;David A. Siler and Chloe Y. Wong,&nbsp;","doi":"10.1021/acs.oprd.4c0036910.1021/acs.oprd.4c00369","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00369https://doi.org/10.1021/acs.oprd.4c00369","url":null,"abstract":"<p >(<i>R</i>)-1-(2,5-Difluoropyridin-3-yl)ethyl(1-methyl-4-(5-(2-(trifluoromethyl)pyrimidine-5-carboxamido)pyridin-2-yl)-1<i>H</i>-1,2,3-triazol-5-yl)carbamate (GS-2278) is a lysophosphatidic acid receptor 1 antagonist under development for the treatment of idiopathic pulmonary fibrosis. GS-2278 is assembled in a 9-step sequence. Initially, 2-bromo-5-fluoropyridine is metalated and trapped with ethyl difluoroacetate. Then, after condensation with tosyl hydrazide, Sakai cyclization with methylamine, and carboxylation with carbon dioxide, the triazole carboxylic acid core is generated. For the final assembly, the core is elaborated through a two-step hydroxamic acid formation and Lossen rearrangement to form an isocyanate which is trapped in situ by a chiral alcohol. The resulting carbamate is Boc-deprotected and subjected to amide coupling with a pyrimidine carboxylic acid to yield the active pharmaceutical ingredient. Process development was conducted to determine reaction and isolation conditions to enable scale-ups to support preclinical and early clinical studies. This paper focuses on the development of conditions from the medicinal chemistry route to the Ph 1 manufacturing route.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"28 11","pages":"4099–4113 4099–4113"},"PeriodicalIF":3.1,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641108","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Development of a Commercial Manufacturing Process for Vepdegestrant, an Orally Bioavailable PROTAC Estrogen Receptor Degrader for the Treatment of Breast Cancer 开发用于治疗乳腺癌的口服生物型 PROTAC 雌激素受体降解剂 Vepdegestrant 的商业制造工艺
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2024-11-05 DOI: 10.1021/acs.oprd.4c0036210.1021/acs.oprd.4c00362
Steve Avery, Jamie M. Buske, Doris Chen, Herman Chen, Xin Chen, Andrew R. Davidson, Jean-Nicolas Desrosiers, Hanqing Dong*, Noalle Fellah, David F. Fernández*, John Grosso, Lu Han, Teri Hochdorfer, Amber M. Johnson, Brian P. Jones, Maciej Kalinowski, Katherine D. Launer-Felty, Jorge Lopez, Teresa Makowski, Carolyn Mastriano, Truong N. Nguyen, Nitinchandra D. Patel, Zhihui Peng*, Tyler Potter, Robert P. Pritchard, Anil M. Rane, Max Reeve, Margaret C. Richins, Chase A. Salazar, John J. Salisbury, Robert Simpson*, Liza Tabshey, Erin J. Tweed, Paul G. Wahome, Nancy Walsh-Sayles, Jordan A. Willie and Ethan Wood, 
{"title":"Development of a Commercial Manufacturing Process for Vepdegestrant, an Orally Bioavailable PROTAC Estrogen Receptor Degrader for the Treatment of Breast Cancer","authors":"Steve Avery,&nbsp;Jamie M. Buske,&nbsp;Doris Chen,&nbsp;Herman Chen,&nbsp;Xin Chen,&nbsp;Andrew R. Davidson,&nbsp;Jean-Nicolas Desrosiers,&nbsp;Hanqing Dong*,&nbsp;Noalle Fellah,&nbsp;David F. Fernández*,&nbsp;John Grosso,&nbsp;Lu Han,&nbsp;Teri Hochdorfer,&nbsp;Amber M. Johnson,&nbsp;Brian P. Jones,&nbsp;Maciej Kalinowski,&nbsp;Katherine D. Launer-Felty,&nbsp;Jorge Lopez,&nbsp;Teresa Makowski,&nbsp;Carolyn Mastriano,&nbsp;Truong N. Nguyen,&nbsp;Nitinchandra D. Patel,&nbsp;Zhihui Peng*,&nbsp;Tyler Potter,&nbsp;Robert P. Pritchard,&nbsp;Anil M. Rane,&nbsp;Max Reeve,&nbsp;Margaret C. Richins,&nbsp;Chase A. Salazar,&nbsp;John J. Salisbury,&nbsp;Robert Simpson*,&nbsp;Liza Tabshey,&nbsp;Erin J. Tweed,&nbsp;Paul G. Wahome,&nbsp;Nancy Walsh-Sayles,&nbsp;Jordan A. Willie and Ethan Wood,&nbsp;","doi":"10.1021/acs.oprd.4c0036210.1021/acs.oprd.4c00362","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00362https://doi.org/10.1021/acs.oprd.4c00362","url":null,"abstract":"<p >A commercial process for vepdegestrant (<b>1</b>), the most advanced PROTAC protein degrader in human clinical trials, has been developed to support clinical and commercial needs. The process features an efficient convergent synthetic strategy through the final reductive amination of two advanced chiral intermediates, as well as several highly efficient telescoped processes and robust crystallization for purity control. The final commercial process of vepdegestrant (<b>1</b>) consists of seven proposed regulatory GMP steps with five isolations in an overall yield of 29%.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"28 11","pages":"4079–4090 4079–4090"},"PeriodicalIF":3.1,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641055","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Continuous Flow Enabled Synthesis of Multiresistant Drug Clofazimine 多耐药性药物氯法齐明的连续流合成
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2024-11-01 DOI: 10.1021/acs.oprd.4c0042010.1021/acs.oprd.4c00420
Rajat Pandey, Faith Akwi and Paul Watts*, 
{"title":"Continuous Flow Enabled Synthesis of Multiresistant Drug Clofazimine","authors":"Rajat Pandey,&nbsp;Faith Akwi and Paul Watts*,&nbsp;","doi":"10.1021/acs.oprd.4c0042010.1021/acs.oprd.4c00420","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00420https://doi.org/10.1021/acs.oprd.4c00420","url":null,"abstract":"<p >Drug resistance to tuberculosis is still one of the major challenges worldwide. Clofazimine, which belongs to the riminophenazine (antibiotic) class, is still one of the active drugs that are efficient against drug-resistant <i>Mycobacterium tuberculosis</i>. Apart from this, it is also a WHO-approved drug for the treatment of leprosy and, at present, is under phase 2 clinical trial for its activity against the SARS-CoV-2 virus. Owing to its vast importance in clinical research, we have developed a semicontinuous flow-mediated synthesis of Clofazimine using readily available <i>p</i>-chloroaniline and 1-fluoro-2-nitrobenzene. The target drug molecule was obtained from four consecutive chemical transformations with nominal residence time, improved purity, and yields when compared to the batch process. Moreover, the first two steps were also successfully telescoped under the optimized reaction conditions.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"28 11","pages":"4163–4172 4163–4172"},"PeriodicalIF":3.1,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.oprd.4c00420","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640955","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
One-Pot Synthesis of Guanidinium 5,5′-Azotetrazolate Avoiding Isolation of Hazardous Sodium 5,5′-Azotetrazolate 避免分离有害的 5,5′-四氮唑钠的 5,5′-四氮唑胍的一锅合成法
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2024-10-30 DOI: 10.1021/acs.oprd.4c0036410.1021/acs.oprd.4c00364
Miroslav Labaj, Zdeněk Jalový*, Robert Matyáš, Jiří Nesveda, Jakub Mikuláštík and Adam Votýpka, 
{"title":"One-Pot Synthesis of Guanidinium 5,5′-Azotetrazolate Avoiding Isolation of Hazardous Sodium 5,5′-Azotetrazolate","authors":"Miroslav Labaj,&nbsp;Zdeněk Jalový*,&nbsp;Robert Matyáš,&nbsp;Jiří Nesveda,&nbsp;Jakub Mikuláštík and Adam Votýpka,&nbsp;","doi":"10.1021/acs.oprd.4c0036410.1021/acs.oprd.4c00364","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00364https://doi.org/10.1021/acs.oprd.4c00364","url":null,"abstract":"<p >Sodium 5,5′-azotetrazolate (Na<sub>2</sub>AzT) is a starting material for various azotetrazole salts that find applications as lead-free primary explosives or high-nitrogen compounds for inflating safety systems (in particular, guanidinium azotetrazolate, GZT). Sodium azotetrazolate, after preparation, is commonly isolated as the pentahydrate, which is relatively safe for handling. But it readily loses hydrate water molecules at higher temperatures or by treatment with organic solvents. In such cases, sensitivity to mechanical stimuli increases considerably and explosion accidents may occur. In this work, the thermal conditions and the role of solvents in water loss from sodium 5,5′-azotetrazolate pentahydrate are presented. Impact and friction sensitivity parameters of the products are described. In the case of guanidinium azotetrazolate, the process for its preparation without producing sodium 5,5′-azotetrazolate is introduced, thus avoiding manipulation of hazardous material and increasing the safety of the procedure.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"28 11","pages":"4091–4098 4091–4098"},"PeriodicalIF":3.1,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.oprd.4c00364","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640724","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Tris(trimethylsilyl)silane in Photochemical Hydrodesulfurization─Methodology and Pyrophoricity 光化学氢化脱硫中的三(三甲基硅基)硅烷--方法和发火性
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2024-10-30 DOI: 10.1021/acs.oprd.4c0041010.1021/acs.oprd.4c00410
Michaela Čierna, Blažej Horváth, Filip Pančík, Michal Šoral, Andrej Kolarovič and Pavol Jakubec*, 
{"title":"Tris(trimethylsilyl)silane in Photochemical Hydrodesulfurization─Methodology and Pyrophoricity","authors":"Michaela Čierna,&nbsp;Blažej Horváth,&nbsp;Filip Pančík,&nbsp;Michal Šoral,&nbsp;Andrej Kolarovič and Pavol Jakubec*,&nbsp;","doi":"10.1021/acs.oprd.4c0041010.1021/acs.oprd.4c00410","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00410https://doi.org/10.1021/acs.oprd.4c00410","url":null,"abstract":"<p >A novel visible-light-induced hydrodesulfurization of a thioacetal was developed. The reaction operates under mild conditions using user-friendly tris(trimethylsilyl)silane as the reductant and a low catalyst loading of photoactive 4CzIPN. The expansion of the reaction scope was thwarted by the operationally hazardous nature of the process, occasionally producing fire. Careful examination of reaction mixtures allowed to identify silane (SiH<sub>4</sub>) as the likely culprit causing the pyrophoricity.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"28 11","pages":"4156–4162 4156–4162"},"PeriodicalIF":3.1,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142641129","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Industrial-Scale Organic Solvent Nanofiltration for Dimer Impurity Removal: Enhancing Vitamin D3 Production 用于去除二聚体杂质的工业级有机溶剂纳滤：提高维生素 D3 的产量
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2024-10-25 DOI: 10.1021/acs.oprd.4c0033310.1021/acs.oprd.4c00333
Jan Schütz, Julia Witte, Maurus Marty and Roman Goy*, 
{"title":"Industrial-Scale Organic Solvent Nanofiltration for Dimer Impurity Removal: Enhancing Vitamin D3 Production","authors":"Jan Schütz,&nbsp;Julia Witte,&nbsp;Maurus Marty and Roman Goy*,&nbsp;","doi":"10.1021/acs.oprd.4c0033310.1021/acs.oprd.4c00333","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00333https://doi.org/10.1021/acs.oprd.4c00333","url":null,"abstract":"<p >This work details the removal of an azine-dimer (AD) impurity from 7-dehydrocholesterol (DHC), a precursor of vitamin D<sub>3</sub>, using a newly developed, sustainable hybrid membrane process, from the idea to implementation. Developed by an international team collaborating under tight time frame and COVID restrictions, this innovative method exemplifies a versatile, energy-saving, and cost-effective separation technology by organic solvent nanofiltration (OSN). Traditional purification methods proved to be unsuccessful, costly, or unsustainable, but this process achieved DHC purification with a minimal yield loss of 0.1%. This separation challenge goes beyond typical OSN applications (solute concentration or solvent exchange) by separating two similar solutes in a solvent mixture. In a three-stage OSN process, the impurity level was reduced from approximately 2600 ppm to below 50 ppm in the final permeate. After developing and scaling up the process, the OSN, precipitation, and filtration units were engineered and constructed. These units were installed in the dsm-firmenich vitamin D<sub>3</sub> plant, and the purification process was successfully commissioned.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"28 11","pages":"4046–4058 4046–4058"},"PeriodicalIF":3.1,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.oprd.4c00333","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142640844","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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