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 5 条

[1] DETERMINATION OF THE ABSOLUTE CONFIGURATION OF OPTICALLY ACTIVE COMPOUNDS BY MEANS OF X-RAYS [J].

BIJVOET, JM ;

PEERDEMAN, AF ;

VANBOMMEL, AJ .

NATURE, 1951, 168 (4268) :271-272

[2] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

[3] An efficient synthesis of optically active metabolites of platelet adhesion inhibitor OPC-29030 by lipase-catalyzed enantioselective transesterification [J].

Kitano, K ;

Matsubara, J ;

Ohtani, T ;

Otsubo, K ;

Kawano, Y ;

Morita, S ;

Uchida, M .

TETRAHEDRON LETTERS, 1999, 40 (28) :5235-5238

[4] 7-chloro-5-hydroxy-1-[2-methyl-4-(2-metaminobenzoyl]-amino)benzoyl]-2,3,4,5-5-tetrahydro-1H-1-benzazepine (OPC-41061):: A potent, orally active nonpeptide arginine vasopressin V2 receptor antagonist [J].

Kondo, K ;

Ogawa, H ;

Yamashita, H ;

Miyamoto, H ;

Tanaka, M ;

Nakaya, K ;

Kitano, K ;

Yamamura, Y ;

Nakamura, S ;

Onogawa, T ;

Mori, T ;

Tominaga, M .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (08) :1743-1754

[5] Synthesis of a key intermediate, (S)-2-[(3-hydroxypropyl)sulfinyl]-1-(o-tolyl)imidazole, for the platelet aggregation inhibitor, OPC-29030 via lipase-catalyzed enantioselective transesterification [J].

Morita, S ;

Matsubara, J ;

Otsubo, K ;

Kitano, K ;

Ohtani, T ;

Kawano, Y ;

Uchida, M .

TETRAHEDRON-ASYMMETRY, 1997, 8 (22) :3707-3710

← 1 →