title: Efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921.
abstract: [reaction: see text] An efficient asymmetric synthesis of the vasopeptidase inhibitor BMS-189921 was accomplished. Two short enantioselective syntheses of the common key intermediate (S)-alpha-aminoazepinone 6b were developed. Olefin 3 was converted to 6b via asymmetric hydrogenation. Alternatively, enyne 12 was converted to racemic alpha-aminoazepinone 15b, which was transformed to 6b by a practical dynamic resolution.
authors.affiliation: Process Research and Development, The Bristol-Myers Squibb Pharmaceutical Research Institute, P.O. Box 4000, Princeton, New Jersey 08543, USA. janak.singh@bms.com
authors.forename: Janak
authors.initials: J
authors.lastname: Singh
authors.forename: David R
authors.initials: DR
authors.lastname: Kronenthal
authors.forename: Mark
authors.initials: M
authors.lastname: Schwinden
authors.forename: Jollie D
authors.initials: JD
authors.lastname: Godfrey
authors.forename: Rita
authors.initials: R
authors.lastname: Fox
authors.forename: Edward J
authors.initials: EJ
authors.lastname: Vawter
authors.forename: Bo
authors.initials: B
authors.lastname: Zhang
authors.forename: Thomas P
authors.initials: TP
authors.lastname: Kissick
authors.forename: Bharat
authors.initials: B
authors.lastname: Patel
authors.forename: Omar
authors.initials: O
authors.lastname: Mneimne
authors.forename: Michael
authors.initials: M
authors.lastname: Humora
authors.forename: Chris G
authors.initials: CG
authors.lastname: Papaioannou
authors.forename: Walter
authors.initials: W
authors.lastname: Szymanski
authors.forename: Michael K Y
authors.initials: MK
authors.lastname: Wong
authors.forename: Chien K
authors.initials: CK
authors.lastname: Chen
authors.forename: James E
authors.initials: JE
authors.lastname: Heikes
authors.forename: John D
authors.initials: JD
authors.lastname: DiMarco
authors.forename: Jun
authors.initials: J
authors.lastname: Qiu
authors.forename: Rajendra P
authors.initials: RP
authors.lastname: Deshpande
authors.forename: Jack Z
authors.initials: JZ
authors.lastname: Gougoutas
authors.forename: Richard H
authors.initials: RH
authors.lastname: Mueller
mesh_terms: D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D004730:Endothelium, Vascular / Q000201:enzymology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D006865:Hydrogenation; D015260:Neprilysin / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
chemical_list: D001381:Azepines; D004791:Enzyme Inhibitors; D015260:Neprilysin; C478302:gemopatrilat