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Flash Thermal Racemization of Chiral Amine in Continuous Flow: An Exploration of Reaction Space Using DoE and Multivariate Transient Flow
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-11 DOI: 10.1021/acs.oprd.4c00508
Matthew J. Takle, Linden Schrecker, Benjamin J. Deadman, Joachim Dickhaut, Andy Wieja, Klaus Hellgardt, King Kuok Mimi Hii
{"title":"Flash Thermal Racemization of Chiral Amine in Continuous Flow: An Exploration of Reaction Space Using DoE and Multivariate Transient Flow","authors":"Matthew J. Takle, Linden Schrecker, Benjamin J. Deadman, Joachim Dickhaut, Andy Wieja, Klaus Hellgardt, King Kuok Mimi Hii","doi":"10.1021/acs.oprd.4c00508","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00508","url":null,"abstract":"The robustness of the flash thermal racemization of optically active 1-phenylethylamine over Pd/γ-Al<sub>2</sub>O<sub>3</sub> was studied by applying split-plot design-of-experiments (DoE), where the effects of temperature, flow rate, and concentration (3-factors) on the e.e. and selectivity (2-responses) were examined and quantified. The same effects were also interrogated using multivariate ramps in transient flow to produce response surfaces for the reaction space. The same set of optimal conditions for the process was identified by both approaches, and the same relationships between the variables were observed: while the extent of racemization (e.e.) can be directly correlated to temperature, a more complex relationship between temperature and flow rate on the selectivity was uncovered.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"121 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143385059","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
Advancing Base Metal Catalysis: Development and Execution of a Ni-catalyzed Borylation/Pd-catalyzed Suzuki Telescoped Process
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-10 DOI: 10.1021/acs.oprd.4c00498
Matthew V. Joannou, Matthew J. Goldfogel, Eric M. Simmons, Steven R. Wisniewski
{"title":"Advancing Base Metal Catalysis: Development and Execution of a Ni-catalyzed Borylation/Pd-catalyzed Suzuki Telescoped Process","authors":"Matthew V. Joannou, Matthew J. Goldfogel, Eric M. Simmons, Steven R. Wisniewski","doi":"10.1021/acs.oprd.4c00498","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00498","url":null,"abstract":"The development and execution of a nickel-catalyzed borylation/palladium-catalyzed Suzuki telescoped process utilizing the inexpensive NiCl<sub>2</sub>·6H<sub>2</sub>O precatalyst for the borylation step are reported. The development of the borylation reaction was guided by a preliminary mechanistic investigation to understand the origin of the dehalogenated side product. The borylation stream was telescoped into a Suzuki coupling to form a bis-heteroaryl bond in the pentacyclic core of afimetoran, an antagonist of toll-like receptors 7/8 (TLR 7/8). The optimization of the Suzuki reaction and kilogram-scale demonstration of the telescoped process showcase the viability of utilizing nickel catalysis in the development of scalable routes to clinical APIs.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143375740","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
Stereoselective Synthesis of Mirogabalin via 1,4-Selective Addition of Lithioacetonitrile to Alkylidene Malonate
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-07 DOI: 10.1021/acs.oprd.4c00510
Hidenori Ochiai, Taiki Mihara, Miwa Sasagawa, Akira Nishiyama
{"title":"Stereoselective Synthesis of Mirogabalin via 1,4-Selective Addition of Lithioacetonitrile to Alkylidene Malonate","authors":"Hidenori Ochiai, Taiki Mihara, Miwa Sasagawa, Akira Nishiyama","doi":"10.1021/acs.oprd.4c00510","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00510","url":null,"abstract":"The synthesis of mirogabalin was studied for industrial production and an alternative to Daiichi–Sankyo’s method was established. The developed synthesis involves the introduction of a two-carbon unit with the stereoselective 1,4-selective addition of lithioacetonitrile to alkylidene malonate and one-carbon degradation by the Hofmann rearrangement. The precursor for the Hofmann rearrangement was readily prepared from the 1,4-adduct via a one-pot reaction involving decarboxylation, hydrolysis, and hydration.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"29 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143258784","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
Systematic Assessment of Calibration Strategies in Spectroscopic Analysis: A Case Study of Paracetamol Crystallization
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-07 DOI: 10.1021/acs.oprd.4c00496
Cha Yong Jong, Geordi Tristan, Lee Jun Jie Felix, Eunice Wan Qi Yeap, Srinivas Reddy Dubbaka, Harsha Nagesh Rao, Shin Yee Wong
{"title":"Systematic Assessment of Calibration Strategies in Spectroscopic Analysis: A Case Study of Paracetamol Crystallization","authors":"Cha Yong Jong, Geordi Tristan, Lee Jun Jie Felix, Eunice Wan Qi Yeap, Srinivas Reddy Dubbaka, Harsha Nagesh Rao, Shin Yee Wong","doi":"10.1021/acs.oprd.4c00496","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00496","url":null,"abstract":"Converting spectral data to concentration is beneficial for effective crystallization process monitoring, enabling timely insights into supersaturation profiles. Calibration models are essential in this process, as they transform spectral information into concentration data. While various calibration strategies exist in the literature, they typically involve three stages: Stage 1 for baseline correction, Stage 2 for regressor selection, and Stage 3 for model form selection. In this study, we systematically evaluated all common strategies within each stage, combining them through a Design of Experiments (DoE) approach using a single paracetamol (PCM) and <i>p</i>-acetoxyacetanilide (PAA) crystallization system. The results showed that Savitzky–Golay Second Derivative (SGSD) performed best for baseline correction (Stage 1), while selecting spectral data from a specific range yielded the highest accuracy in regressor selection (Stage 2). For model selection (Stage 3), Partial Least Squares Regression (PLSR), Principal Component Regression (PCR), and Artificial Neural Network (ANN) were assessed with three optimized models deployed to monitor four crystallization runs in real time. During deployment, PLSR demonstrated the most moderate concentration prediction. However, when comparing all three model forms, the standard deviation of predicted concentrations ranged from 4% to 6% for PCM and 10% to 30% for PAA, with similar performance across all models. Validation against offline High-Performance Liquid Chromatography (HPLC) data showed relative errors of 0–12% for PCM, while PAA predictions had higher errors ranging from 0 to 50<sup>+</sup>%, largely due to PAA’s lower concentration range (10–20 g/L) compared to that of PCM (100–350 g/L). These findings indicate that while online models provide useful real-time approximations, precise measurements still require offline validation.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"11 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143367290","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
Enhancing the Asymmetric Hydrogenation/Desymmetrization of an Achiral Lactone in the Synthesis of (+)-Biotin
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-06 DOI: 10.1021/acs.oprd.4c00359
Werner Bonrath, Roman Goy, Achim Link, Felix Spindler, Jonathan A. Medlock, Marc-André Müller
{"title":"Enhancing the Asymmetric Hydrogenation/Desymmetrization of an Achiral Lactone in the Synthesis of (+)-Biotin","authors":"Werner Bonrath, Roman Goy, Achim Link, Felix Spindler, Jonathan A. Medlock, Marc-André Müller","doi":"10.1021/acs.oprd.4c00359","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00359","url":null,"abstract":"(+)-Biotin plays an essential role as a cofactor in many biological systems and is used to supplement the diets of humans and animals. One of the most elegant chemical production processes involves the asymmetric hydrogenation/desymmetrization of a <i>meso</i>-anhydride to yield the key lactone intermediate. However, relatively high catalyst loadings limit the attractiveness of this route. A number of strategies have been investigated to improve the efficiency of the hydrogenation process, and an improved two-step process has been developed, which significantly reduces the amount of expensive chiral catalyst required and pairs this with a cheap, readily available nickel catalyst, producing the key chiral lactone without a reduction in the enantioselectivity.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"62 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143258785","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
Flow Chemistry for Flowing Cross-Couplings: A Concise Overview
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-06 DOI: 10.1021/acs.oprd.4c00457
Antonella Ilenia Alfano, Simona Barone, Margherita Brindisi
{"title":"Flow Chemistry for Flowing Cross-Couplings: A Concise Overview","authors":"Antonella Ilenia Alfano, Simona Barone, Margherita Brindisi","doi":"10.1021/acs.oprd.4c00457","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00457","url":null,"abstract":"Cross-coupling reactions have revolutionized synthetic chemistry by significantly expanding the scope of carbon–carbon (C–C) and carbon–heteroatom bond formation, making them invaluable tools in the design and synthesis of pharmaceuticals, natural products, and advanced materials. Despite recent advancements in making these reactions more sustainable, some challenges remain, such as the requirement for high temperatures and extended reaction times. In recent decades, flow chemistry has emerged as a powerful solution, with microreactor technology offering numerous advantages for cross-coupling reactions. These include improved reaction efficiency, better heat and mass transfer, and the potential for more environmentally friendly conditions. This review aims to provide a concise and up-to-date guide on recent advancements in flow chemistry as applied to Pd-catalyzed cross-coupling reactions, including Suzuki, Heck, Sonogashira, Negishi, Stille, and Buchwald couplings. By presenting unified schemes for these reactions, the aim of this review is to provide quick and helpful comparisons to readers in order to select optimal reaction conditions based on their starting materials, streamlining the decision-making process in synthetic chemistry.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"13 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192383","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 Scalable Synthesis of Casdatifan (AB521), a Potent, Selective, Clinical-Stage Inhibitor of HIF-2α
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-05 DOI: 10.1021/acs.oprd.4c00497
Clayton Hardman, Artur K. Mailyan, Guillaume Mata, Joel W. Beatty, Samuel L. Drew, Jeremy Fournier, Jaroslaw Kalisiak, Brandon R. Rosen, Matthew Epplin, Balint Gal, Kai Yu, Zhang Wang, Karl Haelsig, Anh Tran, Manmohan R. Leleti, Jay P. Powers, Kenneth V. Lawson
{"title":"Development of a Scalable Synthesis of Casdatifan (AB521), a Potent, Selective, Clinical-Stage Inhibitor of HIF-2α","authors":"Clayton Hardman, Artur K. Mailyan, Guillaume Mata, Joel W. Beatty, Samuel L. Drew, Jeremy Fournier, Jaroslaw Kalisiak, Brandon R. Rosen, Matthew Epplin, Balint Gal, Kai Yu, Zhang Wang, Karl Haelsig, Anh Tran, Manmohan R. Leleti, Jay P. Powers, Kenneth V. Lawson","doi":"10.1021/acs.oprd.4c00497","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00497","url":null,"abstract":"Casdatifan (AB521) is a potent and selective inhibitor of HIF-2α, currently under clinical evaluation for the treatment of clear cell renal cell carcinoma (ccRCC). Here, we report the development of a scalable synthesis of casdatifan, which was used to support its preclinical characterization and the initiation of phase 1 clinical studies. A convergent approach to assembling the tetracyclic scaffold and the development of efficient routes to key intermediates enabled the successful delivery of material to meet clinical development timelines. Crucial to the efficiency of the synthesis was the strategic design of synthetic routes that leverage a combination of substrate and catalyst control to set each of the 5 stereocenters found in the molecule with exquisite selectivity.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"76 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143124956","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 and Scale-Up of an Enabling Synthetic Route to KTX-005, a Muscarinic Acetylcholine Receptor Agonist for the Potential Treatment of Schizophrenia 开发和推广用于潜在治疗精神分裂症的肌卡因乙酰胆碱受体激动剂 KTX-005 的有利合成路线
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-05 DOI: 10.1021/acs.oprd.4c00531
Hanchao Zheng, Rui Zhang, Michel Leeman, Christopher R. H. Hale, Giorgio Attardo, Vijaya B. Gondi
{"title":"Development and Scale-Up of an Enabling Synthetic Route to KTX-005, a Muscarinic Acetylcholine Receptor Agonist for the Potential Treatment of Schizophrenia","authors":"Hanchao Zheng, Rui Zhang, Michel Leeman, Christopher R. H. Hale, Giorgio Attardo, Vijaya B. Gondi","doi":"10.1021/acs.oprd.4c00531","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00531","url":null,"abstract":"Development and optimization of phase-appropriate synthetic technologies to prepare <b>KTX-005</b>, a potent muscarinic acetylcholine receptor agonist, are described in this article. The modular strategy involves three building blocks: commercially available materials dichlorothiadiazole (<b>21</b>), butanethiol (<b>22</b>), and custom-synthesized azabicyclo derivative (<b>18</b>). The highlight of the enabling synthetic strategy toward <b>KTX-005</b> is a unique thiadiazole ring opening/closing sequence to facilitate both dichlorothiadiazole desymmetrization with butanethiol as well as functionalization of the azabicyclo ring derivative <b>18</b>.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"37 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143192676","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
Glass-Facilitated Thermal Decomposition of Difluoromethoxy Arenes
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-04 DOI: 10.1021/acs.oprd.4c00490
Sirun Yang, Tianhua Tang, Hayden Cheek, Joseph J. Topczewski, Eric Wiensch, Daniel J. Valco
{"title":"Glass-Facilitated Thermal Decomposition of Difluoromethoxy Arenes","authors":"Sirun Yang, Tianhua Tang, Hayden Cheek, Joseph J. Topczewski, Eric Wiensch, Daniel J. Valco","doi":"10.1021/acs.oprd.4c00490","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00490","url":null,"abstract":"This report describes a comprehensive differential scanning calorimetry (DSC) evaluation of difluoromethoxy-containing aromatic building blocks. Central to this evaluation is a comparison between DSC thermograms obtained in a glass capillary and those obtained in a gold-plated crucible. The decomposition of difluoromethoxybenzene is shown to be autocatalytic in a glass capillary. A diverse series of difluoromethoxy arenes were evaluated, and most exhibited dichotomous, vessel-dependent decomposition. This distinction raises concerns about glass-facilitated thermal decomposition and safety concerns regarding materials of reactor construction. This study underscores the importance of reactive chemistry evaluations in the development of new fluorinated chemicals, especially when using glass equipment.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"25 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143084017","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 Synthesis of 1,3,2-Dioxathiolane 2,2-Dioxide (DTD) by Hydrogen Peroxide with Titanium Silicalite-1 Catalyst Using a Fixed-Bed Reactor
IF 3.4 3区 化学
Organic Process Research & Development Pub Date : 2025-02-03 DOI: 10.1021/acs.oprd.4c00482
Zunchao Liu, Tianlai Wang, Jianing Li, Xiangmin Tian, Cunfei Ma, Jingnan Zhao, Qingwei Meng
{"title":"Continuous Synthesis of 1,3,2-Dioxathiolane 2,2-Dioxide (DTD) by Hydrogen Peroxide with Titanium Silicalite-1 Catalyst Using a Fixed-Bed Reactor","authors":"Zunchao Liu, Tianlai Wang, Jianing Li, Xiangmin Tian, Cunfei Ma, Jingnan Zhao, Qingwei Meng","doi":"10.1021/acs.oprd.4c00482","DOIUrl":"https://doi.org/10.1021/acs.oprd.4c00482","url":null,"abstract":"1,3,2-Dioxathiolane 2,2-dioxide (DTD) plays a significant role as an electrolyte additive in lithium-ion batteries. It can enhance battery performance, stability, and safety. Additionally, it is a commonly used hydroxylation reagent in organic chemistry. This paper presents a highly efficient, safe preparation, and environmentally friendly continuous DTD synthesis process that does not require catalyst separation. A fixed-bed reactor was constructed with spherical TS-1 as the catalyst and H<sub>2</sub>O<sub>2</sub> as the oxidizer. Under optimized reaction conditions, efficient oxidation of ethylene sulfite (ES) was achieved using dimethyl carbonate as a solvent. The process involved controlling the reaction temperatures at gradients of 10 and 5 °C, respectively, maintaining a molar ratio of H<sub>2</sub>O<sub>2</sub> to substrate of 1.05:1, a liquid hourly space velocity of 0.6 h<sup>–1</sup>, and using a 30 wt % concentration of H<sub>2</sub>O<sub>2</sub> at a substrate concentration of 1 mol/L. The conversion rate was up to 99.5%, and the selectivity of DTD was 99.1%. To prevent hydrolysis of DTD, a continuous separation operation was initiated immediately after the completion of the reaction, and the yield of DTD reached 96%. The successful application of this process not only improves the production efficiency of DTD and reduces the production cost but also establishes the foundation for the industrialized continuous production of DTD.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"30 1","pages":""},"PeriodicalIF":3.4,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143083857","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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