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

Luo-Ting Yu, Ji-Ling Huang, Ching-Yao Chang, Teng-Kuei Yang
2006 Molecules  
A formal enantioselective synthesis of benazepril·HCl (4), an antihypertensive drug, is reported. Our synthesis employed an asymmetric aza-Michael addition of L-homophenylalanine ethyl ester (LHPE, 1) to 4-(2-nitrophenyl)-4-oxobut-2-enoic acid methyl ester (6) as the key step to prepare (2S,3'S)-2-(2-oxo-2,3,4,5tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester (8), which is the key intermediate leading to benazepril·HCl (4).
doi:10.3390/11080641 pmid:17971736 fatcat:x7pr5p4spbb5flbsqgefunwl74