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

[1] Enantioselective synthesis of the metabolites of vasopressin V2 receptor antagonist OPC-31260 via lipase-catalyzed transesterification
Matsubara, J
Kitano, K
Otsubo, K
Kawano, Y
Ohtani, T
Bando, M
Kido, M
Uchida, M
Tabusa, F
TETRAHEDRON, 2000, 56 (27) : 4667 - 4682
[2] An efficient synthesis of a key intermediate for vasopressin V2 receptor agonist OPC-51803 by lipase-catalyzed enantioselective transesterification
Ohtani, T
Kitano, K
Matsubara, J
Morita, S
Kawano, Y
Komatsu, M
Bando, M
Kido, M
Uchida, M
Tabusa, F
HETEROCYCLES, 2002, 58 : 635 - 643
[3] Practical synthesis of both enantiomers of vasopressin V2 receptor antagonist OPC-41061 using the catalytic asymmetric hydrogenation
Yamashita, H
Ohtani, T
Morita, S
Otsubo, K
Kan, K
Matsubara, J
Kitano, K
Kawano, Y
Uchida, M
Tabusa, F
HETEROCYCLES, 2002, 56 (1-2) : 123 - 128
[4] Effectiveness of vasopressin V2 receptor antagonists OPC-31260 and OPC-41061 on polycystic kidney disease development in the PCK
Wang, XF
Gattone, V
Harris, PC
Torres, VE
JOURNAL OF THE AMERICAN SOCIETY OF NEPHROLOGY, 2005, 16 (04): : 846 - 851
[5] Tolvaptan (OPC-41061), a V2 vasopressin receptor antagonist, protects against the decline in renal function observed with loop diuretic therapy
Burnett, JC
Costello-Boerrigter, LC
Smith, WB
Ouyang, J
Zimmer, CA
Orlandi, C
CIRCULATION, 2003, 108 (17) : 398 - 398
[6] Tolvaptan (OPC-41061), a V2 vasopressin receptor antagonist, enhances aquaresis and renal hemodynamics compared to furosemide in mild to moderate heart failure
Costello-Boerrigter, LC
Burnett, JC
Smith, WB
Ouyang, J
Zimmer, CA
Orlandi, C
EUROPEAN HEART JOURNAL, 2004, 25 : 451 - 451
[7] Effects of tolvaptan (OPC-41061), a vasopressin V2 receptor antagonist, and furosemide on hemodynamics, renal functions, serum electrolytes, and neurohormones in dogs with and without heart failure
Onogawa, T
Yamamura, Y
Nakamura, S
Nakayama, S
Fujiki, H
Mori, T
CIRCULATION, 2004, 110 (17) : 21 - 21
[8] An efficient synthesis of a metabolite of vasopressin V2 receptor antagonist, OPC-31260, by metalloporphyrin-catalyzed demethylation
Kawano, Y
Otsubo, K
Matsubara, J
Kitano, K
HETEROCYCLES, 1999, 50 (01) : 17 - 20
[9] Effects of the V2-receptor antagonist OPC-41061 and the loop diuretic furosemide alone and in combination in rats
Hirano, T
Yamamura, Y
Nakamura, S
Onogawa, T
Mori, T
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2000, 292 (01): : 288 - 294
[10] An efficient synthesis of optically active metabolites of platelet adhesion inhibitor OPC-29030 by lipase-catalyzed enantioselective transesterification
Kitano, K
Matsubara, J
Ohtani, T
Otsubo, K
Kawano, Y
Morita, S
Uchida, M
TETRAHEDRON LETTERS, 1999, 40 (28) : 5235 - 5238

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