An efficient asymmetric approach to the R-enantiomer impurity of esomeprazole-Reference-Cited by-同舟云学术

An efficient asymmetric approach to the R-enantiomer impurity of esomeprazole

Published:2016-02-01 Issue:1 Volume:22 Page:17-19
ISSN:2191-0197
Container-title:Heterocyclic Communications
language:
Short-container-title:

Author:

Zhou Guobin¹,Guan Yueqing²

Affiliation:

1. 1Department of Chemistry, Taizhou University, Taizhou 318000, China, Zhejiang Yongtai Technology Co., Ltd., Linhai 317016, China

2. 2Department of Biological and Chemical Engineering, Taizhou Vocational and Technical College, Taizhou 318000, China

Abstract

AbstractEsomeprazole {(S)-5-methoxy-2-[(4-methoxy-3, 5-dimethyl-2-pyridinylmethyl) sulfinyl]-1H-benzimidazole} is a proton pump inhibitor used as an antiulcer drug. Its R-enantiomer 3 was synthesized with high enantioselectivity by asymmetric oxidation of prochiral sulfide 2 using the oxaziridinium salt 4. Product 3, useful as a reference for the quality control of esomeprazole, was characterized by 1H and 13C NMR, IR, and HRMS. The enantiomeric excess was determined by HPLC.

Publisher

Walter de Gruyter GmbH

Subject

Organic Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/hc-2015-0101/pdf

Reference30 articles.

1. Synthesis of chiral sulfoxides by metal - catalyzed oxidation witht - butyl hydroperoxide Synthesis;Di Furia,1984

2. Von New compounds useful for the synthesis of and omeprazole and a process for their preparation US;Unge,2005

3. An efficient asymmetric oxidation of sulfides to sulfoxiues;Pitchen;Tetrahedron Lett,1984

4. Del Highly enantioselective oxidation of sulfides to sulfoxides by a new oxaziridinium salt;Rio;Lett,2007

5. Lars Enantiomeric separation of omeprazole and its metabolite hydroxyomeprazole using non - aqueous capillary electrophoresis;Olsson;Chromatogr,2006

Cited by 1 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Research Progress in the Synthesis of Benzo[d]pentamembered Heterocyclic Thioethers Containing Two Heteroatoms;Chinese Journal of Organic Chemistry;2024