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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,*
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. 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.

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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