(3R,5S)-5-(((S)-1-amino-2-(3-fluorophenyl)ethyl)dihydro-3-(3-hydroxy-3-methylbutyl)furan-2(3H)one) p-toluenesulfonic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,5S)-5-(((S)-1-amino-2-(3-fluorophenyl)ethyl)dihydro-3-(3-hydroxy-3-methylbutyl)furan-2(3H)one) p-toluenesulfonic acid
• 英文别名: (3R,5S)-5-[(1S)-1-amino-2-(3-fluorophenyl)ethyl]-3-(3-hydroxy-3-methylbutyl)oxolan-2-one;4-methylbenzenesulfonic acid
• 化学式: C₇H₈O₃S*C₁₇H₂₄FNO₃
• 分子量: 481.586
• InChiKey: QSKCJWKXCZNAMF-WEMUQIOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R,5S)-5-(((S)-1-amino-2-(3-fluorophenyl)ethyl)dihydro-3-(3-hydroxy-3-methylbutyl)furan-2(3H)one) p-toluenesulfonic acid 、 2-喹喔啉羧酸 在 N,N'-羰基二咪唑 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以70.2%的产率得到CP 481715
  参考文献：
  名称：

  Process Development of CP-481715, a Novel CCR1 Antagonist

  摘要：

  Process development for the synthesis of 2-quinoxalinecarboxamide, N-[(1S,2S,4R)-4-(aminocarbonyl)-1-[(3-fluorophenyl)methyl]-2,7-dihydroxy-7-methyloctyl] is described. An optimized,and streamlined process starting from lactone 2 was developed: Lactone 2 was alkylated diastereoselectively with prenyl bromide, followed by deprotection of the N-Boc group and concomitant hydration of the olefin. Aminolysis of the lactone in methanolic ammonia afforded the titled compound.

  DOI：

  10.1021/op050059w
• 作为产物：
  描述：

  tert-butyl (S)-2-(3-fluorophenyl)-1-((2S,4R)-tetrahydro-4-(3-methylbut-2-enyl)-5-oxofuran-2-yl)ethylcarbamate 在 磷酸 作用下， 以 甲苯 为溶剂， 反应 19.0h， 生成 (3R,5S)-5-(((S)-1-amino-2-(3-fluorophenyl)ethyl)dihydro-3-(3-hydroxy-3-methylbutyl)furan-2(3H)one) p-toluenesulfonic acid
  参考文献：
  名称：

  Process Development of CP-481715, a Novel CCR1 Antagonist

  摘要：

  Process development for the synthesis of 2-quinoxalinecarboxamide, N-[(1S,2S,4R)-4-(aminocarbonyl)-1-[(3-fluorophenyl)methyl]-2,7-dihydroxy-7-methyloctyl] is described. An optimized,and streamlined process starting from lactone 2 was developed: Lactone 2 was alkylated diastereoselectively with prenyl bromide, followed by deprotection of the N-Boc group and concomitant hydration of the olefin. Aminolysis of the lactone in methanolic ammonia afforded the titled compound.

  DOI：

  10.1021/op050059w

文献信息

• Org. Process Res. Dev. 2005, 9, 466-471
  作者：

  DOI：——

  日期：——