Enantioselective resolution of 4-chloromandelic acid by liquid-liquid extraction using 2-chloro-N-carbobenzyloxy-L-amino acid

被引：6

作者：

Lu, Ruichen ^{[1
]}

He, Quan ^{[2
]}

Feng, Cai ^{[1
]}

Peng, Yangfeng ^{[1
]}

机构：

[1] East China Univ Sci & Technol, Sch Chem Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China

[2] Dalhousie Univ, Dept Engn, Fac Agr, Truro, NS, Canada

来源：

CHIRALITY | 2017年 / 29卷 / 11期

关键词：

2-chloro-N-carbobenzyloxy-L-amino acid; 4-chloromandelic acid; chiral separation; liquid-liquid extraction; N-(2-chlorobenzyloxy)-succinimide; valine; CHIRAL STATIONARY-PHASE; MANDELIC-ACID; MOBILE-PHASE; SEPARATION; ENANTIOMERS; ENANTIOSEPARATION; DERIVATIVES; CHROMATOGRAPHY; SELECTOR; CYCLODEXTRIN;

D O I：

10.1002/chir.22738

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A liquid-liquid extraction resolution of 4-chloro-mandelic acid (4-ClMA) was studied by using 2-chloro-N-carbobenzyloxy-L-amino acid (2-Cl-Z-AA) as a chiral extractant. Important factors affecting the extraction efficiency were investigated, including the type of chiral extractant, pH value of aqueous phase, initial concentration of chiral extractant in organic phase, initial concentration of 4-ClMA in aqueous phase, and resolution temperature. It was observed that the concentration of (R)-4-ClMA was much higher than that of (S)-4-ClMA in organic phase due to a higher stability of the complex formed between (R)-4-ClMA and 2-Cl-Z-AA. A separation factor () of 3.05 was obtained at 0.02 mol/L 2-Cl-Z-Valine dissolved in dichloromethane, pH of 2.0, concentration of 4-ClMA of 0.11 mmol/Land T of 296.7K.

引用

页码：708 / 715

页数：8

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