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Paper | Special issue | Vol 54, No. 1, 2001, pp.131-138
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S(I)2
An Efficient Synthesis of Optical Isomers of Vasopressin V2 Receptor Antagonist OPC-41061 by Lipase-catalyzed Enantioselective Transesterification

Jun Matsubara,* Seiji Morita, Hiroshi Yamashita, Kenji Otsubo, Kazuyoshi Kitano, Tadaaki Ohtani, Yoshikazu Kawano, Masahiko Bando, Masaru Kido, Minoru Uchida, and Fujio Tabusa

*Medical Chemistry Research Institute, Otsuka Pharmaceutical Co., Ltd., Kagasuno 463-10, Kawauchi-cho, Tokushima, Tokushima 771-0192, Japan


The optically active enantiomers of 7-chloro-5-hydroxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (OPC-41061, 1) were enantioselectively synthesized. The chiral acetate ((R)-(–)-3) and the chiral alcohol ((S)-(+)-2) were prepared via the resolution of the racemic alcohol ((±)-2) using the lipase-mediated transesterification with vinyl acetate. Compounds ((R)-(–)-3) and ((S)-(+)-2) were converted to optically active 1.