OPTICAL RESOLUTION BY PREFERENTIAL CRYSTALLIZATION OF 2-(3,4-CARBONYLDIOXYPHENYL)-2-(PHTHALIMIDOOXY)ACETIC ACID, A KEY INTERMEDIATE OF CEPHALOSPORIN ANTIBIOTIC M-14659

被引：3

作者：

MURAKAMI, K ^{[1
]}

OHASHI, M ^{[1
]}

MATSUNAGA, A ^{[1
]}

YAMAMOTO, I ^{[1
]}

TOMIGUCHI, A ^{[1
]}

NOHIRA, H ^{[1
]}

机构：

[1] MOCHIDA PHARMACEUT CO LTD, FUJI CENT RES LAB, 722 JIMBA AZA UENOHARA, GOTEMBA, SHIZUOKA 412, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1992年 / 65卷 / 12期

关键词：

D O I：

10.1246/bcsj.65.3288

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(+/-)-2-(3,4-Carbonyldioxyphenyl)-2-(phthalimidooxy)acetic acid [(+/-)-1] was efficiently resolved into a pair of optically active forms by preferential crystallization. Successive preferential crystallization of (+/-)-1 was experimented at 15-degrees-C under stirring in acetone, and (+)- and (-)-1 with optical purity of 68-85% were obtained. The racemization of (-)-1 proceeded smoothly in the presence of triethylamine to give (+/-)-1 which was reusable for the preferential crystallization procedure. A potent antipseudomonal cephalosporin M-14659 (2) was prepared from (+)-1.

引用

页码：3288 / 3293

页数：6

共 12 条

[1] SYNTHESIS OF ALPHA-HYDROXYARYLACETIC ACIDS FROM BROMOFORM ARYLALDEHYDES AND POTASSIUM HYDROXIDE WITH LITHIUM CHLORIDE CATALYST [J].