1-tert-butyl 2-methyl (2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidine-1,2-dicarboxylate | 1361054-82-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-tert-butyl 2-methyl (2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidine-1,2-dicarboxylate
• 英文别名: 1-O-tert-butyl 2-O-methyl (2S,4S)-4-(4-pyrimidin-2-ylpiperazin-1-yl)pyrrolidine-1,2-dicarboxylate
• CAS: 1361054-82-1
• 化学式: C₁₉H₂₉N₅O₄
• 分子量: 391.47
• InChiKey: IODOLBVKCZCNCX-GJZGRUSLSA-N

物化性质

• 沸点：
  519.9±60.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 2-methyl (2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidine-1,2-dicarboxylate 在 盐酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 (3,3-二氟吡咯烷-1-基)[(2S,4S)-4-[4-(嘧啶-2-基)哌嗪-1-基]吡咯烷-2-基]甲酮
  参考文献：
  名称：

  New Synthetic Route to a Dipeptidyl Peptidase-4 Inhibitor

  摘要：

  A new synthetic route to a dipeptidyl peptidase-4 (DPP4) inhibitor was developed and demonstrated on a multigram scale. This approach takes advantage of the cheap and readily available Boc-trans-4-hydroxy-L-proline methyl ester as starting material which was derivatized through an S(N)2 reaction. Several leaving groups were studied, and the nosylate group showed superiority over other derivatives. Formation of an amide using the most costly starting material, 3,3-difluoropyrrolidine, was performed late in the synthesis to minimize its economical impact on the overall cost of the API.

  DOI：

  10.1021/op200309z
• 作为产物：
  描述：

  1-(2-嘧啶基)哌嗪 、 1-(1,1-dimethylethyl) 2-methyl (2S,4R)-4-{[(4-nitrophenyl)sulfonyl]oxy}-2,3,4,5-tetrahydro-1H-pyrrole-1,2-dicarboxylate 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以95%的产率得到1-tert-butyl 2-methyl (2S,4S)-4-(4-(pyrimidin-2-yl)piperazin-1-yl)pyrrolidine-1,2-dicarboxylate
  参考文献：
  名称：

  New Synthetic Route to a Dipeptidyl Peptidase-4 Inhibitor

  摘要：

  A new synthetic route to a dipeptidyl peptidase-4 (DPP4) inhibitor was developed and demonstrated on a multigram scale. This approach takes advantage of the cheap and readily available Boc-trans-4-hydroxy-L-proline methyl ester as starting material which was derivatized through an S(N)2 reaction. Several leaving groups were studied, and the nosylate group showed superiority over other derivatives. Formation of an amide using the most costly starting material, 3,3-difluoropyrrolidine, was performed late in the synthesis to minimize its economical impact on the overall cost of the API.

  DOI：

  10.1021/op200309z