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Design and process study of chiral separation of (2S,4S)-1-(tert-butoxy carbonyl)-4-(methoxymethyl) pyrrolidine-2-carboxylic acid for green manufacturing

文献类型：期刊论文

作者Ge, Shuwang3; Fu, Mingwei1,3; Gu, Dihai3; Wei, Lai3; Qian, Kun2; Rui, Qi1; Ma, Yan1; Li, Liang1; Wang, Huaiqiu1; Li, Lingchao4
刊名GREEN CHEMISTRY
出版日期2024-01-12
页码11
ISSN号1463-9262
DOI10.1039/d3gc04435a
通讯作者Wang, Yihong(yihongwang@seu.edu.cn)
英文摘要An effective approach to separate chiral (2S,4S)-1-(tert-butoxy carbonyl)-4-(methoxymethyl) pyrrolidine-2-carboxylic acid ((2S,4S)-TBMP)) from mixed (2S,4S)-TBMP and (2S,4R)-1-(tert-butoxy carbonyl)-4-(methoxymethyl) pyrrolidine-2-carboxylic acid ((2S,4R)-TBMP), an important intermediate for the anti-HCV drug Velpatasvir, was developed for the first time, eliminating the need for salinization and dissociation processes and several organic solvents with water. Conceivable binding modes were set up by Gaussian calculation, and the separation process was designed and studied based on the calculation. The results showed that only the monohydrate of (2S,4S)-TBMP could be crystallized since three hydrogen bonds were formed between (2S,4S)-TBMP and water, which resulted in more stability and isomer separation. Compared to the original approach, our new approach exhibits a remarkable 17.4% increase in yield, a 43.3% rise in atom economy (AE), a 43.3% improvement in reaction mass efficiency (RME), and a substantial 32.0 g g(-1) reduction in process mass intensity (PMI). An industrial-scale implementation was set up successfully according to the new approach, achieving a batch capacity of 100 kg.
WOS关键词VELPATASVIR ; SOFOSBUVIR ; ENANTIOMERS ; HCV ; RESOLUTION ; METRICS
资助项目Priority Academic Program Development of Jiangsu Higher Education Institutions[8507048423] ; School of Chemistry and Chemical Engineering, Southeast University ; Nanjing Zenji Research Laboratories[81571812] ; National Natural Science Foundation of China[1107047002] ; Priority Academic Program Development of Jiangsu Higher Education Institutions[BK20220314] ; Priority Academic Program Development of Jiangsu Higher Education Institutions[2275122] ; Priority Academic Program Development of Jiangsu Higher Education Institutions[2275123] ; Natural Science Foundation of Jiangsu Province
WOS研究方向Chemistry ; Science & Technology - Other Topics
语种英语
出版者ROYAL SOC CHEMISTRY
WOS记录号WOS:001146789200001
源URL[http://119.78.100.183/handle/2S10ELR8/308775]  
专题中国科学院上海药物研究所
通讯作者Wang, Yihong
作者单位1.Nanjing Zenji Res Labs, Nanjing 211800, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
3.Southeast Univ, Sch Chem & Chem Engn, Nanjing 211189, Peoples R China
4.Jiangsu Zenji Pharmaceut Ltd, Huaian 223100, Peoples R China
推荐引用方式
GB/T 7714		 Ge, Shuwang,Fu, Mingwei,Gu, Dihai,et al. Design and process study of chiral separation of (2S,4S)-1-(tert-butoxy carbonyl)-4-(methoxymethyl) pyrrolidine-2-carboxylic acid for green manufacturing[J]. GREEN CHEMISTRY,2024:11.
APA Ge, Shuwang.,Fu, Mingwei.,Gu, Dihai.,Wei, Lai.,Qian, Kun.,...&Wang, Yihong.(2024).Design and process study of chiral separation of (2S,4S)-1-(tert-butoxy carbonyl)-4-(methoxymethyl) pyrrolidine-2-carboxylic acid for green manufacturing.GREEN CHEMISTRY,11.
MLA Ge, Shuwang,et al."Design and process study of chiral separation of (2S,4S)-1-(tert-butoxy carbonyl)-4-(methoxymethyl) pyrrolidine-2-carboxylic acid for green manufacturing".GREEN CHEMISTRY (2024):11.

入库方式： OAI收割

来源：上海药物研究所

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