ANALYSIS OF WARFARIN ENANTIOMERS - CHROMATOGRAPHIC-SEPARATION OF 6 STEREOISOMERIC ESTERS PREPARED FROM (-)-(1S,2R,4R)-ENDO-1,4,5,6,7,7-HEXACHLOROBICYCLO[2,2,1]HEPT-5-ENE-2-CARBOXYLIC ACID

被引：3

作者：

DUKE, CC ^{[1
]}

CARTER, SR ^{[1
]}

HAMBLEY, TW ^{[1
]}

HOLDER, GM ^{[1
]}

CUTLER, DJ ^{[1
]}

机构：

[1] UNIV SYDNEY,SCH CHEM,SYDNEY,NSW 2006,AUSTRALIA

来源：

CHIRALITY | 1994年 / 6卷 / 08期

关键词：

CHIRAL CYCLIC HEMIKETAL DERIVATIVES NMR DATA; CRYSTAL STRUCTURE ELUCIDATION; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY (HPLC); QUININE SALT RESOLUTION OF; RAC-ENDO-1,4,5,6,7,7-HEXACHLOROBICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLIC ACID; PREPARATIVE RESOLUTION OF RAC-WARFARIN AND RAC-P-CHLOROWARFARIN; REACTION MECHANISM;

D O I：

10.1002/chir.530060812

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Reaction of rac-warfarin, (-)-(1S, 2R, 4R)-endo-1, 4, 5, 6, 7, 7-hexachlorobicyclo[2.2.1]hept-5-ene-2-carboxylic acid [(-)-HCA] and carbodiimide reagents gave two noncyclic ketonic diastereoisomeric derivatives whereas rac-warfarin and (-)-HCA acid chloride with 4-(dimethylamino)pyridine gave four cyclic hemiketal diastereoisomeric ester derivatives, The structure and stereochemistry of diastereoisomeric esters prepared from warfarin and p-chlorowarfarin were determined from H-1- and C-13-NMR spectra, mass spectra, and hydrolysis to warfarin and p-chlorowarfarin enantiomers, The structure and stereochemistry of one of the cyclic hemiketal diastereoisomeric derivatives of warfarin are supported by an X-ray crystallographic determination, Mechanisms for the formation of all products are proposed. (C) 1994 Wiley-Liss, Inc.

引用

页码：670 / 680

页数：11

共 19 条

[11] OPTICAL RESOLUTION OF RACEMIC DRUGS BY CHIRAL HPLC ON CELLULOSE AND AMYLOSE TRIS(PHENYLCARBAMATE) DERIVATIVES [J].