title: Formal synthesis of the ACE inhibitor benazepril x HCl via an asymmetric aza-Michael reaction.
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 x HCl (4).
authors.affiliation: Laboratory of Organometallic Chemistry, East China University of Science & Technology, Shanghai, 200237, P.R. China.
authors.forename: Luo-Ting
authors.initials: LT
authors.lastname: Yu
authors.forename: Ji-Ling
authors.initials: JL
authors.lastname: Huang
authors.forename: Ching-Yao
authors.initials: CY
authors.lastname: Chang
authors.forename: Teng-Kuei
authors.initials: TK
authors.lastname: Yang
mesh_terms: D000806:Angiotensin-Converting Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D012997:Solvents / Q000737:chemistry
chemical_list: D000806:Angiotensin-Converting Enzyme Inhibitors; D001552:Benzazepines; D012997:Solvents; C044946:benazepril