A Novel Chiral Resolving Reagent, Bis((S)-Mandelic acid)-3-nitrophthalate, for Amlodipine Racemate Resolution: Scalable Synthesis and Resolution Process

被引：19

作者：

Lee, Hong Woo ^{[1
]}

Shin, Sung Jae ^{[1
]}

Yu, Hosung ^{[1
]}

Kang, Sung Kwon ^{[1
]}

Yoo, Choong Leol ^{[1
]}

机构：

[1] Chong Kun Dang Res Inst, Chem Res Lab, Cheonan 330831, South Korea

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2009年 / 13卷 / 06期

关键词：

DERIVATIVES;

D O I：

10.1021/op900070c

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel bis((S)-mandelic acid)-3-nitrophthalate (1), a chiral resolving reagent for the separation of (S)-(-)-isomers of amlodipine from the racemate thereof, is designed and synthesized. A simple three-step pilot-scale preparation of 1, along with the optimization of a resolution process on the racemate amlodipine, is reported.

引用

页码：1382 / 1386

页数：5

共 11 条

[1] LONG-ACTING DIHYDROPYRIDINE CALCIUM-ANTAGONISTS .1. 2-ALKOXYMETHYL DERIVATIVES INCORPORATING BASIC SUBSTITUENTS [J].

ARROWSMITH, JE ;

CAMPBELL, SF ;

CROSS, PE ;

STUBBS, JK ;

BURGES, RA ;

GARDINER, DG ;

BLACKBURN, KJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (09) :1696-1702

[2]

ARROWSMITH JE, 1989, Patent No. 9522301

[3]

BRUGGINK A, 1997, CHIRALITY IND, V2, P81

[4]

BYUN IS, 2008, Patent No. 2008026838

[5]

CHOUNG YS, 2007, Patent No. 7202365

[6] Dimethyl sulfoxide (DMSO) waste residues and municipal waste water odor by dimethyl sulfide (DMS): the North-East WPCP Plant of Philadelphia [J].

Glindemann, D ;

Novak, J ;

Witherspoon, J .

ENVIRONMENTAL SCIENCE & TECHNOLOGY, 2006, 40 (01) :202-207

[7] DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF THE ACTIVE AMLODIPINE ENANTIOMER AS (-)-S - A CORRECTION [J].

GOLDMANN, S ;

STOLTEFUSS, J ;

BORN, L .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (18) :3341-3344

[8] 1,4-DIHYDROPYRIDINES - EFFECTS OF CHIRALITY AND CONFORMATION ON THE CALCIUM-ANTAGONIST AND CALCIUM AGONIST ACTIVITIES [J].

GOLDMANN, S ;

STOLTEFUSS, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1559-1578

[9] Diastereospecific intramolecular Ullmann couplings:: Unique chiral auxiliary for the preparation of 3,3′-disubstituted MeO-BIPHEP derivatives [J].

Gorobets, E ;

McDonald, R ;

Keay, BA .

ORGANIC LETTERS, 2006, 8 (07) :1483-1485

[10]

KIM JS, 2008, Patent No. 20080249314

← 1 2 →