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Cu-Catalyzed Coupling of Aryl Halides Utilizing Ammonia and Hydroxypicolinamide Ligands 利用氨和羟基喹啉酰胺配体铜催化芳基卤化物的偶联
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-05-15 DOI: 10.1021/acs.oprd.5c00101
David J. Bernhardson, Ian Hotham, Liam S. Sharninghausen, Robert A. Singer, Daniel W. Widlicka
{"title":"Cu-Catalyzed Coupling of Aryl Halides Utilizing Ammonia and Hydroxypicolinamide Ligands","authors":"David J. Bernhardson, Ian Hotham, Liam S. Sharninghausen, Robert A. Singer, Daniel W. Widlicka","doi":"10.1021/acs.oprd.5c00101","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00101","url":null,"abstract":"The hydroxypicolinamide family of ligands has previously demonstrated utility in Cu-catalyzed C–N couplings and hydroxylation of heteroaryl halides. The application of these ligands has been extended to the coupling of ammonia with aryl bromides and iodides using the dimethoxy picolinamide scaffold ligand. By tailoring reaction conditions, Cu-DMPS provides high reactivity and selectivity toward amination over hydroxylation. Utilizing aqueous ammonia or anhydrous ammonia with K<sub>3</sub>PO<sub>4</sub> in MeOH provides robust conversion of bromides and iodides to the corresponding aryl amines. Additionally, this catalytic system gives efficient C–N couplings with simple primary amines by using the same general reaction conditions.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"28 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144000662","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
Enabling the First Scale-Up of the Selective HER2 Inhibitor BI-4142 选择性HER2抑制剂BI-4142的首次规模化应用
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-05-14 DOI: 10.1021/acs.oprd.5c00127
Eugene Chong, Ruoshi Li, Weitong Dong, Maxim Chevliakov, Thomas G. Tampone, Yongda Zhang, Bo Qu, Nizar Haddad, Jon C. Lorenz, Max Sarvestani, Thuraya Omar, Huayu Li, Joe J. Gao, Donghong A. Gao, Scott Pennino, Ling Wu, Earl Spinelli, Steven Yao, Heewon Lee, Frederic Buono, Jinhua J. Song, Birgit Wilding
{"title":"Enabling the First Scale-Up of the Selective HER2 Inhibitor BI-4142","authors":"Eugene Chong, Ruoshi Li, Weitong Dong, Maxim Chevliakov, Thomas G. Tampone, Yongda Zhang, Bo Qu, Nizar Haddad, Jon C. Lorenz, Max Sarvestani, Thuraya Omar, Huayu Li, Joe J. Gao, Donghong A. Gao, Scott Pennino, Ling Wu, Earl Spinelli, Steven Yao, Heewon Lee, Frederic Buono, Jinhua J. Song, Birgit Wilding","doi":"10.1021/acs.oprd.5c00127","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00127","url":null,"abstract":"The enabling synthesis of the first route to HER2 inhibitor <b>BI-4142</b> (<b>1</b>) to deliver a drug substance in kilogram quantity is reported. The synthetic route involves (1) a fit-for-purpose synthesis of pyrimido[5,4-<i>d</i>]pyrimidine <b>2</b>; (2) a high yielding, scalable synthesis of aniline <b>3</b>; (3) a safer sodium tungstate-catalyzed sulfide oxidation; (4) S<sub>N</sub>Ar reactions to form C–N bonds; and (5) amidation via Schotten–Baumann conditions. With the speed of delivery prioritized, a purification protocol using silica gel filtration and crystallizations was developed in time to control the quality of API. The overall yield of the delivery route was improved from 22% to 46% over a prior route starting from <b>2</b>.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"11 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143945805","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
Scalable Membrane Enabled One-Pot Liquid-Phase Oligonucleotide Synthesis 可扩展膜支持一锅液相寡核苷酸合成
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-05-13 DOI: 10.1021/acs.oprd.5c00117
Ronan Kelly, Catalina Parga, Steven Ferguson
{"title":"Scalable Membrane Enabled One-Pot Liquid-Phase Oligonucleotide Synthesis","authors":"Ronan Kelly, Catalina Parga, Steven Ferguson","doi":"10.1021/acs.oprd.5c00117","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00117","url":null,"abstract":"In this article, a new one-pot liquid-phase oligonucleotide synthesis (OP-LPOS) route enabled by organic solvent resistant (OSR) ceramic membranes is described. This approach was demonstrated through the synthesis of 6mer and 18mer 2’-OMe phosphorothioate oligonucleotides with high stepwise filtration yields (97–100%), and high crude purity (∼72% for 18mer) using just 1.5 equiv of phosphoramidites. Ceramic organic solvent nanofiltration (OSN) and ultrafiltration (OSU) membranes were used to selectively retain the growing oligonucleotide, which is reversibly tethered to a 4-arm branched PEG support, facilitating lower molecular weight reaction byproducts to permeate to waste. This is the first application of ceramic ultrafiltration membranes in such an application, which enables purification of intermediate products in just 5 diavolumes with high permeance (13 Lm<sup>–2</sup> h<sup>–1</sup> bar<sup>–1</sup>). We employ a one-pot approach that integrates sequential coupling, sulfurization, and detritylation steps, followed by a single membrane purification step per chain extension cycle. Analysis of the methodology indicates that the homogeneous reactions and separation performance, which use commercially available reagents and highly scalable membrane systems, represent a promising alternative to solid-phase oligonucleotide synthesis (SPOS) for large-scale manufacturing of therapeutic oligonucleotides. Furthermore, the combination of OP-LPOS with membrane separation increases intermediate product purity and yield. It reduces the number of unit operations, cycle times, and process mass intensity (PMI) compared to the previous state-of-the-art membrane-based LPOS.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"115 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143946210","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
Green Chemistry Articles of Interest to the Pharmaceutical Industry 制药工业感兴趣的绿色化学文章
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-05-10 DOI: 10.1021/acs.oprd.5c00050
Melissa A. Ashley, Miles H. Aukland, Marian C. Bryan, Megan A. Cismesia, Theresa Dutschei, Oliver D. Engl, Pascal S. Engl, Álvaro Enríquez García, Alejandro Gimenez Molina, Vanessa Harawa, George Karageorgis, Shazia Keily, Christopher B. Kelly, Alexandre Leclair, Johnny W. Lee, Wei Li, Matthew Osborne, Jan Pawlas, Paul F. Richardson, Samuel C. Scott, Alan Steven, Balaram S. Takale, Mingshuo Zeng
{"title":"Green Chemistry Articles of Interest to the Pharmaceutical Industry","authors":"Melissa A. Ashley, Miles H. Aukland, Marian C. Bryan, Megan A. Cismesia, Theresa Dutschei, Oliver D. Engl, Pascal S. Engl, Álvaro Enríquez García, Alejandro Gimenez Molina, Vanessa Harawa, George Karageorgis, Shazia Keily, Christopher B. Kelly, Alexandre Leclair, Johnny W. Lee, Wei Li, Matthew Osborne, Jan Pawlas, Paul F. Richardson, Samuel C. Scott, Alan Steven, Balaram S. Takale, Mingshuo Zeng","doi":"10.1021/acs.oprd.5c00050","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00050","url":null,"abstract":"This article has not yet been cited by other publications.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"33 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-05-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143931230","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
Preparation of Furazan Carboxylates from Enamines by a Nitrosation–Oxidative Cyclization Sequence 胺基亚硝化-氧化环化法制备呋喃唑羧酸酯
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-05-09 DOI: 10.1021/acs.oprd.5c00119
Connor L. Martin, Matthew E. Martinez
{"title":"Preparation of Furazan Carboxylates from Enamines by a Nitrosation–Oxidative Cyclization Sequence","authors":"Connor L. Martin, Matthew E. Martinez","doi":"10.1021/acs.oprd.5c00119","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00119","url":null,"abstract":"We report a telescoped nitrosation–oxidative cyclization sequence for preparing furazan (1,2,5-oxadiazole) carboxylic esters from the corresponding enamines. This method is mainly suitable for preparing furazan carboxylates substituted with aromatic rings. Preliminary process safety screening shows that our method offers advantages compared to the common dioxime dehydration method for preparing furazans.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"126 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-05-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143930692","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 Broadly Applicable Enzymatic Ligation Process for the Production of Single Guide RNAs 一种广泛应用于生产单个引导rna的酶连接工艺的发展
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-05-05 DOI: 10.1021/acs.oprd.4c00502
Martina Bigatti, André Moser, Bas Dierssen, Shtjefen Frrokaj, Elena Covato, Christophe Pfleger, Joerg Lill, Yael Leiser, Joël Zuber, Andreas Staempfli, Filippo Sladojevich, Stefan G. Koenig
{"title":"Development of a Broadly Applicable Enzymatic Ligation Process for the Production of Single Guide RNAs","authors":"Martina Bigatti, André Moser, Bas Dierssen, Shtjefen Frrokaj, Elena Covato, Christophe Pfleger, Joerg Lill, Yael Leiser, Joël Zuber, Andreas Staempfli, Filippo Sladojevich, Stefan G. Koenig","doi":"10.1021/acs.oprd.4c00502","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00502","url":null,"abstract":"In this manuscript, we present a robust chemo-enzymatic approach for the production of single guide RNAs (sgRNAs), essential reagents for CRISPR-Cas9-based cell and gene therapy applications currently under development. Our method leverages ligase-mediated assembly of two RNA fragments, each synthesized using standard solid-phase chemistry. This versatile process has been applied, without modification, to produce a variety of GMP-grade sgRNAs, supporting our clinical <i>ex vivo</i> cell therapy pipeline. We demonstrate that our approach consistently achieves higher purity (10–15% improvement in LC-UV area%) and significantly greater yield (3–4 times higher) compared to traditional linear solid-phase synthesis, which is commonly used for sgRNA production. Importantly, the process utilizes T4 RNA ligase 2, a natural, nonengineered enzyme, which can be easily sourced from several vendors. We believe that openly sharing this method will drive significant progress in the development of cell and gene therapies, enabling the production of higher-quality sgRNAs at lower cost, ultimately improving accessibility and treatment outcomes for patients.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"88 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143910237","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 Broadly Applicable Enzymatic Ligation Process for the Production of Single Guide RNAs 一种广泛应用于生产单个引导rna的酶连接工艺的发展
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2025-05-05 DOI: 10.1021/acs.oprd.4c0050210.1021/acs.oprd.4c00502
Martina Bigatti, André Moser, Bas Dierssen, Shtjefen Frrokaj, Elena Covato, Christophe Pfleger, Joerg Lill, Yael Leiser, Joël Zuber, Andreas Staempfli, Filippo Sladojevich* and Stefan G. Koenig*, 
{"title":"Development of a Broadly Applicable Enzymatic Ligation Process for the Production of Single Guide RNAs","authors":"Martina Bigatti,&nbsp;André Moser,&nbsp;Bas Dierssen,&nbsp;Shtjefen Frrokaj,&nbsp;Elena Covato,&nbsp;Christophe Pfleger,&nbsp;Joerg Lill,&nbsp;Yael Leiser,&nbsp;Joël Zuber,&nbsp;Andreas Staempfli,&nbsp;Filippo Sladojevich* and Stefan G. Koenig*,&nbsp;","doi":"10.1021/acs.oprd.4c0050210.1021/acs.oprd.4c00502","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00502https://doi.org/10.1021/acs.oprd.4c00502","url":null,"abstract":"<p >In this manuscript, we present a robust chemo-enzymatic approach for the production of single guide RNAs (sgRNAs), essential reagents for CRISPR-Cas9-based cell and gene therapy applications currently under development. Our method leverages ligase-mediated assembly of two RNA fragments, each synthesized using standard solid-phase chemistry. This versatile process has been applied, without modification, to produce a variety of GMP-grade sgRNAs, supporting our clinical <i>ex vivo</i> cell therapy pipeline. We demonstrate that our approach consistently achieves higher purity (10–15% improvement in LC-UV area%) and significantly greater yield (3–4 times higher) compared to traditional linear solid-phase synthesis, which is commonly used for sgRNA production. Importantly, the process utilizes T4 RNA ligase 2, a natural, nonengineered enzyme, which can be easily sourced from several vendors. We believe that openly sharing this method will drive significant progress in the development of cell and gene therapies, enabling the production of higher-quality sgRNAs at lower cost, ultimately improving accessibility and treatment outcomes for patients.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 5","pages":"1228–1236 1228–1236"},"PeriodicalIF":3.1,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144067686","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
Preparation of Impurity-Spiked Good Laboratory Practice Toxicological Batches of Active Pharmaceutical Ingredient Using Resonant Acoustic Mixing 用共振声混合法制备掺有杂质的良好实验室操作规范的原料药毒理学批
IF 3.1 3区 化学
Organic Process Research & Development Pub Date : 2025-05-03 DOI: 10.1021/acs.oprd.5c0006910.1021/acs.oprd.5c00069
Dane Holte*, Keith C. Coffman, Darryl D. Dixon, Elizabeth Horstman, Anuradha Jamwal, Seung Moh Koo, David A. Siler, Eric A. Standley and Anna M. Wagner, 
{"title":"Preparation of Impurity-Spiked Good Laboratory Practice Toxicological Batches of Active Pharmaceutical Ingredient Using Resonant Acoustic Mixing","authors":"Dane Holte*,&nbsp;Keith C. Coffman,&nbsp;Darryl D. Dixon,&nbsp;Elizabeth Horstman,&nbsp;Anuradha Jamwal,&nbsp;Seung Moh Koo,&nbsp;David A. Siler,&nbsp;Eric A. Standley and Anna M. Wagner,&nbsp;","doi":"10.1021/acs.oprd.5c0006910.1021/acs.oprd.5c00069","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00069https://doi.org/10.1021/acs.oprd.5c00069","url":null,"abstract":"<p >Gilead process chemistry has recently started to employ resonant acoustic mixing (RAM) technology to produce impurity-spiked good laboratory practice (GLP) toxicology batches of active pharmaceutical ingredient (API). When compared to other methods of generating impurity-spiked API, the benefits of this process are operational simplicity and reproducibility, solvent-free mixing and homogenization, ability to maintain the crystalline form of the API, and minimization of occupational exposure to powdered API. In this work, we describe a typical RAM process used to generate a GLP toxicology batch of API, including starting point instrument settings and the use of ceramic beads to homogenize material.</p>","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 5","pages":"1311–1316 1311–1316"},"PeriodicalIF":3.1,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144067682","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
Preparation of Impurity-Spiked Good Laboratory Practice Toxicological Batches of Active Pharmaceutical Ingredient Using Resonant Acoustic Mixing 用共振声混合法制备掺有杂质的良好实验室操作规范的原料药毒理学批
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-05-03 DOI: 10.1021/acs.oprd.5c00069
Dane Holte, Keith C. Coffman, Darryl D. Dixon, Elizabeth Horstman, Anuradha Jamwal, Seung Moh Koo, David A. Siler, Eric A. Standley, Anna M. Wagner
{"title":"Preparation of Impurity-Spiked Good Laboratory Practice Toxicological Batches of Active Pharmaceutical Ingredient Using Resonant Acoustic Mixing","authors":"Dane Holte, Keith C. Coffman, Darryl D. Dixon, Elizabeth Horstman, Anuradha Jamwal, Seung Moh Koo, David A. Siler, Eric A. Standley, Anna M. Wagner","doi":"10.1021/acs.oprd.5c00069","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00069","url":null,"abstract":"Gilead process chemistry has recently started to employ resonant acoustic mixing (RAM) technology to produce impurity-spiked good laboratory practice (GLP) toxicology batches of active pharmaceutical ingredient (API). When compared to other methods of generating impurity-spiked API, the benefits of this process are operational simplicity and reproducibility, solvent-free mixing and homogenization, ability to maintain the crystalline form of the API, and minimization of occupational exposure to powdered API. In this work, we describe a typical RAM process used to generate a GLP toxicology batch of API, including starting point instrument settings and the use of ceramic beads to homogenize material.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"24 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143910419","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
Efficient Synthesis of Crisaborole from m-Cresol: A Practical and Scalable Process 间甲酚高效合成Crisaborole：一种实用且可扩展的工艺
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-05-02 DOI: 10.1021/acs.oprd.5c00075
Chunxiao Wang, Yuanming Jiang, Hongsen Zhang, Xiaonan Liu, Kangjie Liu, Chao Li, Renzhong Qiao
{"title":"Efficient Synthesis of Crisaborole from m-Cresol: A Practical and Scalable Process","authors":"Chunxiao Wang, Yuanming Jiang, Hongsen Zhang, Xiaonan Liu, Kangjie Liu, Chao Li, Renzhong Qiao","doi":"10.1021/acs.oprd.5c00075","DOIUrl":"https://doi.org/10.1021/acs.oprd.5c00075","url":null,"abstract":"Herein, process improvement work on the phosphodiesterase-4 inhibitor crisaborole is described. The starting material 2-bromo-5-hydroxybenzaldehyde was replaced with the low-cost <i>m</i>-cresol. The process involves the purification of the low-melting-point bromophenol by a cocrystal strategy, selective debromination of the <i>gem</i>-dibromide byproduct, boronation through a telescoped process, and design of experiments optimization in the active pharmaceutical ingredient (API) synthesis stage. The economic, efficient, and practical synthesis of crisaborole was successfully achieved. It is worth noting that filtration unit operations were applied in the scale-up process of Miyaura borylation to address the common issue of incomplete conversion in this process.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"70 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143897883","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
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