ethyl (2E)-3-[(4S,5R)-N-(tert-butoxycarbonyl)-4-methyl-5-(trifluoromethyl)oxazolidin-2-on-5-yl]-prop-2-enoate | 1160175-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: ethyl (2E)-3-[(4S,5R)-N-(tert-butoxycarbonyl)-4-methyl-5-(trifluoromethyl)oxazolidin-2-on-5-yl]-prop-2-enoate
• CAS: 1160175-75-6
• 化学式: C₁₅H₂₀F₃NO₆
• 分子量: 367.322
• InChiKey: ZSVKEMFDIJHLAW-GVKXJSCCSA-N

反应信息

• 作为产物：
  描述：

  ethyl (2E,4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-4-(trifluoromethyl)hex-2-enoate 、 N,N'-羰基二咪唑 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以48%的产率得到ethyl (2E)-3-[(4S,5R)-N-(tert-butoxycarbonyl)-4-methyl-5-(trifluoromethyl)oxazolidin-2-on-5-yl]-prop-2-enoate
  参考文献：
  名称：

  Amino Acid-Based Synthesis of Trifluoromethylalkene Dipeptide Isosteres by Alcohol-Assisted Nucleophilic Trifluoromethylation and Organozinc−Copper-Mediated S_N2′ Alkylation

  摘要：

  A novel synthetic approach to Xaa-Yaa-type (Z)-trifluoromethylalkene dipeptide isostere (CF3-ADI) has been developed. Starting from readily available L-phenylalanine and L-alanine, several CF3-ADIs were obtained through nucleophilic trifluoromethylation of gamma-keto esters and S(N)2' alkylation of trifluoromethylated mesylates. The influence of a trifluoromethyl group on the diastereoselectivity of the S(N)2' reaction is also discussed.

  DOI：

  10.1021/jo9005602