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(3S)-3-(叔丁氧羰基氨基)-4-氧代丁酸甲酯的合成 被引量：1

Synthesis of Methyl(3S)-3-(tert-Butoxycarbonylamino)-4-oxobutanoate
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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%。 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%.
作者 郭锦材 张拥军 张兴贤
机构地区 浙江工业大学药学院 浙江普洛医药科技有限公司
出处 《中国医药工业杂志》 CAS CSCD 北大核心 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)
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 sitagliptin type 1I diabetes intermediate methyl （3S）-3-（tert-butoxycarbonylamino）-4-oxobutanoate synthesis
分类号 O625 [理学—有机化学]
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参考文献10

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二级参考文献15

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共引文献11

同被引文献11

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  • 3Ramalingam K, Woodard R W. Synthesis of stereospecific deu- terium-labeled homoserines and homoscdne lactonesI-J. J Org Chem, 1988, 53(9) :1900-1903.
  • 4Markidis T, Kokotos G. A novel approach to the synthesis of chiral terminal 1,2-diamines[J]. J 0rg Chem, 2001, 66 (5) : 1919-1923.
  • 5Anelli P L, Biffi C, Montanafi F, et al. Fast and selective oxi- dation of primary alcohols to aldehydes or to carboxylic acids and of secondary alcohols to ketones mediated by oxoammonium salts under two-phase conditions[J], J org Chem, 1987, 52 (12) .. 2559-2562.
  • 6朱国良,张健,杨立军,等.西他列汀中间体及其制备方法和用途[P].WO20110305725,2011-03-31.
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  • 8Ahlfors J E, Mekouar K. Selective caspasc inhibitors and uses there of[P]. WO 2009140765, 2009-11-26.
  • 9Alan J H, Shin M S, ]un M A, et al. Synthesis biological evalua- tion and structural determination of/?-aminoacylcontaining cyclic hydrazine derivatives as dipeptidyl peptidase IV(DPP-N) inhib- itors[J]. Bioorg Med Chem Lett,2007,17(9):2622-2628.
  • 10孙桂芳,蔡正艳,周伟澄.西他列汀合成路线图解[J].中国医药工业杂志,2008,39(5):383-386. 被引量：12

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中国医药工业杂志
2012年 第3期

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