| 侯茜茜,冯双双,张明云.西他列汀关键中间体2,4,5-三氟苯乙酸的合成研究[J].安徽医药,2019,23(8):1513-1515. |
| 西他列汀关键中间体2,4,5-三氟苯乙酸的合成研究 |
| Study on the synthesis of 2,4,5-trifluorophenylacetic for the key intermediates of sitagliptin |
| 投稿时间：2018-01-25 |
| DOI： |
| 中文关键词: 二肽基肽酶Ⅳ抑制剂 糖尿病,2型 化学技术,合成 2,4,5-三氟苯乙酸 2,3,5-三氟苯胺 西他列汀 工业化生产 |
| 英文关键词: Dipeptidyl-peptidase IV inhibitors Diabetes mellitus,type 2 Chemistry techniques,synthetic 2,4,5-trifluorophenylacetic 2,3,5-trifluoroanilineation Sitagliptin Industrial production |
| 基金项目: |
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| 中文摘要: |
| 目的 探讨西他列汀的关键中间体2,4,5-三氟苯乙酸的设计和合成。方法 以2,3,5-三氟苯胺为原料,先经过重氮化还原得到1,2,4-三氟苯,再经液溴和三氯化铝的作用下发生亲电取代,得到2,4,5-三氟溴苯,最后经丙二酸二乙酯缩合,再经氢氧化钠水解、盐酸酸化、加热脱羧得到纯品2,4,5-三氟苯乙酸。结果 产品经过核磁氢谱和核磁碳谱表征,纯品2,4,5-三氟苯乙酸总收率达到54%。结论 该路线能有效减少副产物,适合工业化生产。 |
| 英文摘要: |
| Objective To study the design and synthesis of 2,4,5-trifluorophenylacetic acid,the key intermediate for the preparation of Sitagliptin. Methods With 2,3,5-trifluoroaniline as raw material,1,2,4-trifluorobenzene was obtained through diazotization,and then electrophilic substitution was conducted under the action of liquid bromine and aluminum trichloride to obtain 2,4,5-trifluorobenzene,which was then condensed with diethyl malonate.Pure 2,4,5-trifluorobenzene was obtained through sodium hydroxide hydrolysis,hydrochloric acid acidification and decarboxylation.Results The structure of the target compound were characterized by 1H NMR and 13C NMR.The total yield was 54% based on 2,4,5-Trifluoroaniline.Conclusion The method can effectively reduce byproducts and is suitable for industrial production. |
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