(3R,7aS)-6-tert-Butoxycarbonylmethyl-5-oxo-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazole-6-carboxylic acid | 479490-43-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3R,7aS)-6-tert-Butoxycarbonylmethyl-5-oxo-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazole-6-carboxylic acid
• 英文别名: (3R,7aS)-6-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-5-oxo-3-phenyl-1,3,7,7a-tetrahydropyrrolo[1,2-c][1,3]oxazole-6-carboxylic acid
• CAS: 479490-43-2
• 化学式: C₁₉H₂₃NO₆
• 分子量: 361.395
• InChiKey: HVVNPLAJXJNUCJ-AVJPJTGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,7aS)-6-tert-Butoxycarbonylmethyl-5-oxo-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazole-6-carboxylic acid 在 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成 tert-butyl 2-((3S,5S)-5-(hydroxymethyl)-2-oxopyrrolidin-3-yl)acetate
  参考文献：
  名称：

  A Practical and Improved Synthesis of (3S,5S)-3-[(tert-Butyloxycarbonyl)methyl]- 5-[(methanesulfonyloxy)methyl]-2- pyrrolidinone

  摘要：

  A practical and improved synthesis of (3S,5S)3- [(tert-butyloxycarbonyl)methyl]-5-[(methanesulfonyloxy)methyl]-2-pyrrolidinone (1) is described. The key transformations involve a highly efficient reaction sequence consisting of ethoxycarbonylation, alkylation, hydrolysis, and decarboxylation to produce compound 10. The process described herein is practical, robust, and cost-effective, and it has been successfully implemented in a pilot plant to produce a multikilogram quantity of mesylate 1.

  DOI：

  10.1021/jo020433f
• 作为产物：
  描述：

  (+)-(3R,7aS)-四氢-3-苯基-3H,5H-吡咯并[1,2-c]噁唑-5-酮 在 sodium hydroxide 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 21.0h， 生成 (3R,7aS)-6-tert-Butoxycarbonylmethyl-5-oxo-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazole-6-carboxylic acid
  参考文献：
  名称：

  A Practical and Improved Synthesis of (3S,5S)-3-[(tert-Butyloxycarbonyl)methyl]- 5-[(methanesulfonyloxy)methyl]-2- pyrrolidinone

  摘要：

  A practical and improved synthesis of (3S,5S)3- [(tert-butyloxycarbonyl)methyl]-5-[(methanesulfonyloxy)methyl]-2-pyrrolidinone (1) is described. The key transformations involve a highly efficient reaction sequence consisting of ethoxycarbonylation, alkylation, hydrolysis, and decarboxylation to produce compound 10. The process described herein is practical, robust, and cost-effective, and it has been successfully implemented in a pilot plant to produce a multikilogram quantity of mesylate 1.

  DOI：

  10.1021/jo020433f