Preparation of (R)-Ethyl 4-Chloro-3-hydroxybutanoate throughEnzymatic Ammonolysis in Organic Media

Abstract

The lipase-catalyzed resolution of ethyl 4-chloro-3-hydroxybutanoate (CHBE) by aminolysis was carried out to prepare (R)-4-chloro-3-hydroxybutanoate. Through screening of lipases, lipase Novozym435 was found to show the highest activity and enantioselectivity for the ammonolysis of CHBE. The effect of different solvents on the ammonolysis was investigated. And 1,4-dioxane was found to be the most optimum solvent. The influence of various factors on the enzymatic resolution was studied. The optimal temperature was 30 ℃. 99% ee value of (R)-CHBE and 57.7% conversion of CHBE could be achieved at 35 h when the concentration of enzyme was 10 mg/mL and the concentration of substrate was 0.5 mol/L.

Key words: 4-chloro-3-hydroxybutanoate, resolution, ammonolysis, lipase

Cite this article

JIN Yong^a,WU Jian-Ping^a,XU Gang^a,YANG Li-Rong*^{,a,b. Preparation of (R)-Ethyl 4-Chloro-3-hydroxybutanoate throughEnzymatic Ammonolysis in Organic Media[J]. Chin. J. Org. Chem., 2006, 26(10): 1384-1388.}

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有机相酶催化氨解反应拆分制备(R)-4-氯-3-羟基丁酸乙酯