An efficient synthesis of optical isomers of vasopressin V2 receptor antagonist OPC-41061 by lipase-catalyzed enantioselective transesterification

被引：16

作者：

Matsubara, J ^{[1
]}

Morita, S ^{[1
]}

Yamashita, H ^{[1
]}

Otsubo, K ^{[1
]}

Kitano, K ^{[1
]}

Ohtani, T ^{[1
]}

Kawano, Y ^{[1
]}

Bando, M ^{[1
]}

Kido, M ^{[1
]}

Uchida, M ^{[1
]}

Tabusa, F ^{[1
]}

机构：

[1] Otsuka Pharmaceut Co Ltd, Med Chem Res Inst, Tokushima 7710192, Japan

来源：

HETEROCYCLES | 2001年 / 54卷 / 01期

关键词：

kinetic resolution; 5-hydroxybenzazepine; enantioselectivity; enantiomeric excess; vinyl acetate;

D O I：

10.3987/COM-99-S(I)2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：131 / 138

页数：8

共 23 条

[21] Long-term oral treatment of a novel, nonpeptide selective vasopressin V2 receptor antagonist, OPC-31260 prolongs the survival in rats treated with adriamycin
Takeuchi, M
Lee, JD
Kawasaki, N
Shimizu, H
Fukumoto, M
Wada, Y
Ueda, T
CIRCULATION, 1998, 98 (17) : 579 - 579
[22] ASYMMETRIC-SYNTHESIS OF A CHIRAL NORBORNENE DERIVATIVE BY LIPASE-CATALYZED TRANSESTERIFICATION OF CIS-ENDO-5-NORBORNENE-2,3-DIMETHANOL AND ITS APPLICATION TO THE SYNTHESIS OF AN OPTICALLY-ACTIVE TXA2 ANTAGONIST
MURATA, M
IKOMA, S
ACHIWA, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (08) : 2329 - 2331
[23] Optical-Controlled Kinetic Switch: Fine-Tuning of the Residence Time of an Antagonist Binding to the Vasopressin V2 Receptor in In Vitro, Ex Vivo, and In Vivo Models of ADPKD
Gu, Xiaoke
Yuan, Haoxing
Zhao, Wenchao
Sun, Nan
Yan, Wenzhong
Jiang, Chunyu
He, Yan
Liu, Hongli
Cheng, Jianjun
Guo, Dong
JOURNAL OF MEDICINAL CHEMISTRY, 2023, 66 (02) : 1454 - 1466

← 1 2 3 →