An efficient procedure for the resolution of α-cyano-α-fluoro-p-tolylacetic acid (CFTA) via the diastereomeric N-carbobenzyloxy-cis-1-amino-2-indanol esters

被引：20

作者：

Fujiwara, T

Sasaki, M

Omata, K

Kabuto, C

Kabuto, K ^{[1
]}

Takeuchi, Y

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan

[2] Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Sugitani, Toyama 9300194, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 03期

关键词：

D O I：

10.1016/j.tetasy.2003.12.024

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Development of a new, efficient resolution method of alpha-cyano-alpha-fluoro-p-tolylacetic acid (CFTA) 2a has been successfully achieved, which has been troublesome to obtain by conventional methods, in spite of its outstanding ability as an NMR chiral derivatizing agent. Fractional recrystallization of a mixture of the diastereomeric CFTA esters prepared from racemic CFTA chloride and (1R,2S)-N-carbobenzyloxy-cis-1-amino-2-indanol (-)-B afforded the less-soluble diastereomer, which was hydrolyzed to give (S)-2a. It has also been demonstrated that optically active N-acetyl-cis-1-amino-2-indanol is effective for the chromatographic resolution of alpha-arylacetic acids including ibuprofen and naproxen. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：555 / 563

页数：9

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