| (3S)-3-(叔丁氧羰基氨基)-4-氧代丁酸甲酯的合成 |
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| 引用本文： | 郭锦材,张拥军,张兴贤.(3S)-3-(叔丁氧羰基氨基)-4-氧代丁酸甲酯的合成[J].中国医药工业杂志,2012,43(3):172-174. |
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| 作者姓名： | 郭锦材 张拥军 张兴贤 |
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| 作者单位： | 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 |
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| 基金项目： | 浙江省自然科学基金项目 |
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| 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%。
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| 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 |
Synthesis of Methyl(3S)-3-(tert-Butoxycarbonylamino)-4-oxobutanoate |
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| Authors: | GUO Jincai ZHANG Yongjun ZHANG Xingxian |
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| Institution: | 1(1.College of Pharmaceutical Sciences,Zhejiang University of Technology,Hangzhou 310032; 2.Zhejiang Apeloa Medical Technology Co.,Ltd.,Dongyang 322118) |
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| Abstract: | Methyl(3S)-3-(tert-butoxycarbonylamino)-4-oxobutanoate,an important chiral intermediate of sitagliptin,was synthesized from L-aspartic acid by selective methylation in the presence of SOCl2 to give 4-methyl L-aspartate hydrochloride,which was subjected to Boc-protection,acylation with ethyl chloroformate and reduction by NaBH4,followed by oxidization by NaClO/TEMPO with an overall yield of about 41%. |
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| Keywords: | sitagliptin type Ⅱ diabetes intermediate methyl(3S)-3-(tert-butoxycarbonylamino)-4-oxobutanoate synthesis |
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