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Optimized Synthesis of a Key Intermediate of Nirmatrelvir

文献类型：期刊论文

作者Qin, Hongjian1,2; Jin, Chen3; Odilov, Abdullajon2,4; Bonku, Emmanuel Mintah2,4; Zhu, Fuqiang5; Liu, Qi5; Shen, Jingshan3,4; Aisa, Haji A.1,2
刊名ORGANIC PROCESS RESEARCH & DEVELOPMENT
出版日期2022-12-20
页码6
ISSN号1083-6160
关键词alpha-cyanomethylation neodymium chloride hydrogenation one-pot cyclic glutamine analog Nirmatrelvir
DOI10.1021/acs.oprd.2c00225
通讯作者Shen, Jingshan(shenjingshan@simm.ac.cn) ; Aisa, Haji A.(haji@ms.xjb.ac.cn)
英文摘要In this study, the development of a concise alternative process for synthesis of a key nirmatrelvir intermediate cyclic glutamine analog is described. The process proceedes via alpha-cyanomethylation of dimethyl N-BocGlu in the presence of NdCl3, followed by one-pot Raney nickel-catalyzed hydrogenation of the cyano group with concomitant cyclization and ammonolysis and subsequent deprotection of N-Boc to deliver the target intermediate cyclic glutamine analog in three steps with an 82% overall yield and 99.4 A% high-performance liquid chromatography (HPLC) purity. This study resulted in improved synthetic efficiency and stereoselectivity of alpha-cyanomethylation for production of a key nirmatrelvir intermediate cyclic glutamine analog.
WOS关键词1,3-ASYMMETRIC INDUCTION ; 3CL PROTEASE ; ACID ; REAGENTS ; POTENT
资助项目West Light Foundation of The Chinese Academy of Sciences[2018-XBYJRC-001] ; 2020 ANSO Collaborative Research Project[ANSO-CR-SP-2020-03]
WOS研究方向Chemistry
语种英语
出版者AMER CHEMICAL SOC
WOS记录号WOS:000903620900001
源URL[http://119.78.100.183/handle/2S10ELR8/304016]  
专题中国科学院上海药物研究所
通讯作者Shen, Jingshan; Aisa, Haji A.
作者单位1.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Reg, Urumqi 830011, Xinjiang, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Jiangsu, Peoples R China
4.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
5.Topharman Shanghai Co Ltd, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714		 Qin, Hongjian,Jin, Chen,Odilov, Abdullajon,et al. Optimized Synthesis of a Key Intermediate of Nirmatrelvir[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT,2022:6.
APA Qin, Hongjian.,Jin, Chen.,Odilov, Abdullajon.,Bonku, Emmanuel Mintah.,Zhu, Fuqiang.,...&Aisa, Haji A..(2022).Optimized Synthesis of a Key Intermediate of Nirmatrelvir.ORGANIC PROCESS RESEARCH & DEVELOPMENT,6.
MLA Qin, Hongjian,et al."Optimized Synthesis of a Key Intermediate of Nirmatrelvir".ORGANIC PROCESS RESEARCH & DEVELOPMENT (2022):6.

入库方式： OAI收割

来源：上海药物研究所

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