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Molecules 2006, 11(8), 641-648; doi:10.3390/11080641
Article

Formal Synthesis of the ACE Inhibitor Benazepril·HCl via an Asymmetric Aza-Michael Reaction

1, 1, 3 and 3,*
1 Laboratory of Organometallic Chemistry, East China University of Science & Technology, Shanghai, 200237, P.R. China 2 Department of Pharmaceutical and Biochemical Engineering, Sichuan University, Sichuan, 610065, P.R. China 3 Department of Chemistry, National Chung-Hsing University, Taichung, 402, Taiwan 4 Department of Biotechnology and Bioinformatics, Asia University, Wufeng, Taichung, 413, Taiwan 5 Wisdom Pharmaceutical Co. Ltd., Haimen, Jiangsu, 226100, P.R. China
* Author to whom correspondence should be addressed.
Received: 26 June 2006 / Revised: 20 July 2006 / Accepted: 23 August 2006 / Published: 23 August 2006
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Abstract

A formal enantioselective synthesis of benazepril·HCl (4), an anti- hypertensive drug, is reported. Our synthesis employed an asymmetric aza-Michael addition of L-homophenylalanine ethyl ester (LHPE, 1) to 4-(2-nitrophenyl)-4-oxo- but-2-enoic acid methyl ester (6) as the key step to prepare (2S,3’S)-2-(2-oxo-2,3,4,5- tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester (8), which is the key intermediate leading to benazepril·HCl (4).
Keywords: Asymmetric Aza-Michael reaction; L-homophenylalanine ethyl ester; benazepril·HCl; ACE inhibitor. Asymmetric Aza-Michael reaction; L-homophenylalanine ethyl ester; benazepril·HCl; ACE inhibitor.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Yu, L.-T.; Huang, J.-L.; Chang, C.-Y.; Yang, T.-K. Formal Synthesis of the ACE Inhibitor Benazepril·HCl via an Asymmetric Aza-Michael Reaction. Molecules 2006, 11, 641-648.

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