(±)-亮氨酸的合成  

Synthesis of (±)-Leucine

作　　者：董菁[1] 邢静[1] 严晶晶[1] 施小新[1] 

机构地区：[1]华东理工大学药学院,上海200237

出　　处：《合成化学》2010年第1期97-98,120,共3页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(20972048);上海市教育发展基金资助项目(03SG27)

摘　　要：以氨基丙二酸二乙酯盐酸盐(2)为原料通过一条全新路线合成了外消旋亮氨酸盐酸盐(1)。2的氨基经Boc保护制得Boc-氨基丙二酸二乙酯(3);3与甲代烯丙基氯发生取代反应制得Boc-氨基-(2-甲基-2-丙烯基)丙二酸二乙酯(4);4经Pd/C催化加氢制得Boc-氨基-(2-异丁基)丙二酸二乙酯(5);5在浓盐酸中回流反应,一步完成脱保护、脱羧、水解过程合成1。总收率55%,其结构经1H NMR和MS确证。A novel synthetic route for racemic leucine hydrochloride （1） starting from diethyl aminomalonate hydrochloride（2） was studied herein. Amino group of 2 was first protected with （Boc）20 to give diethyl N-Boc-amino-malonate, then treated with 3-chloro-2-methylprop-1-ene to produce diethyl N-Boc-amino-2-（2-methyl-2-propenyl）-malonate（4）. Pd/C catalyzed hydrogenation of double bond of 4 yielded diethyl N-Boc-amino-2-isobutyl-malonate（5）. 1 in overall yield of 55% was synthesized from 5 by one-pot of deprotection, decarboxylation and hydrolysis in concentrated hydrochloric acid at reflux refluxing. The structures were confirmed by ^1H NMR and MS

关 键 词：亮氨酸 亮氨酸盐酸盐 合成 

分 类 号：O629.71[理学—有机化学]