(3S)-3-(叔丁氧羰基氨基)-4-氧代丁酸甲酯的合成  

Synthesis of Methyl(3S)-3-(tert-Butoxycarbonylamino)-4-oxobutanoate

作　　者：郭锦材[1] 张拥军 张兴贤[1] 

机构地区：[1]浙江工业大学药学院,浙江杭州310032 [2]浙江普洛医药科技有限公司,浙江东阳322118

出　　处：《中国医药工业杂志》2012年第3期172-174,共3页Chinese Journal of Pharmaceuticals

基　　金：浙江省自然科学基金项目(Y4100692)

摘　　要：L-门冬氨酸在氯化亚砜作用下选择性甲酯化生成L-门冬氨酸-4-甲酯盐酸盐,经二碳酸二叔丁酯保护氨基、与氯甲酸乙酯成混酐后经硼氢化钠还原得到(3S)-3-(叔丁氧羰基氨基)-4-羟基丁酸甲酯,最后经NaClO/TEMPO氧化得到西他列汀重要手性中间体(3S)-3-(叔丁氧羰基氨基)-4-氧代丁酸甲酯,总收率约41%。Methyl （3S）-3-（tert-butoxycarbonylamino）-4-oxobutanoate, an important chiral intermediate ot sitagliptin, was synthesized from L-aspartic acid by selective methylation in the presence of SOC12 to give 4-methyl L-aspartate hydrochloride, which was subjected to Boc-protection, acylation with ethyl chloroformate and reduction by NaBH,, followed by oxidization by NaC10/TEMPO with an overall yield of about 41%.

关 键 词：西他列汀 2型糖尿病 中间体 (3S)-3-(叔丁氧羰基氨基)-4-氧代丁酸甲酯 合成 

分 类 号：O625[理学—有机化学]