Article ; Online: Formal synthesis of the ACE inhibitor benazepril x HCl via an asymmetric aza-Michael reaction.
Molecules (Basel, Switzerland)
2006 Volume 11, Issue 8, Page(s) 641–648
Abstract: ... Our synthesis employed an asymmetric aza-Michael addition of L-homophenylalanine ethyl ester (LHPE, 1) to 4-(2 ... leading to benazepril x HCl (4). ...
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). |
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MeSH term(s) | Angiotensin-Converting Enzyme Inhibitors/chemical synthesis ; Angiotensin-Converting Enzyme Inhibitors/chemistry ; Benzazepines/chemical synthesis ; Benzazepines/chemistry ; Models, Chemical ; Solvents/chemistry |
Chemical Substances | Angiotensin-Converting Enzyme Inhibitors ; Benzazepines ; Solvents ; benazepril (UDM7Q7QWP8) |
Language | English |
Publishing date | 2006-08-23 |
Publishing country | Switzerland |
Document type | Journal Article |
ZDB-ID | 1413402-0 |
ISSN | 1420-3049 ; 1431-5165 ; 1420-3049 |
ISSN (online) | 1420-3049 |
ISSN | 1431-5165 ; 1420-3049 |
DOI | 10.3390/11080641 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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