An efficient synthesis of optical isomers of vasopressin V-2 receptor antagonist OPC-41061 by lipase-catalyzed enantioselective transesterification

Authors
Matsubara, J Morita, S Yamashita, H Otsubo, K Kitano, K Ohtani, T Kawano, Y Bando, M Kido, M Uchida, M Tabusa, F
Citation
J. Matsubara et al., An efficient synthesis of optical isomers of vasopressin V-2 receptor antagonist OPC-41061 by lipase-catalyzed enantioselective transesterification, HETEROCYCLE, 54(1), 2001, pp. 131-138
Citations number
5
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
54
Issue
1
Year of publication
2001
Pages
131 - 138
Database
ISI
SICI code
0385-5414(20010101)54:1<131:AESOOI>2.0.ZU;2-V
Abstract
The optically active enantiomers of 7-chloro-5-hydroxy-1-[2-methyl-4-(2-met hylbenzoylamino)benzoyl] -2,3,4,5-tetrahydro-1H-1-benzazepine (OPC-41061, 1 ) were enantioselectively synthesized. The chiral acetate ((R)-(-)-3) and t he chiral alcohol ((S)-(+)-2) were prepared via the resolution of the racem ic alcohol ((+/-)-2) using the lipase-mediated transesterification with vin yl acetate. Compounds ((R)-(-)-3) and ((S)-(+)-2) were converted to optical ly active 1.