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

doi:10.3390/11080641

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

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

Luo-Ting Yu¹, Ji-Ling Huang¹, Ching-Yao Chang³ and Teng-Kuei Yang^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; in revised form: 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.

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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.

AMA 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(8):641-648.

Chicago/Turabian Style

Yu, Luo-Ting; Huang, Ji-Ling; Chang, Ching-Yao; Yang, Teng-Kuei. 2006. "Formal Synthesis of the ACE Inhibitor Benazepril·HCl via an Asymmetric Aza-Michael Reaction." Molecules 11, no. 8: 641-648.

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