methyl (R)-N-(ethoxycarbonyl)-phenylglycinate | 161533-37-5

• 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: methyl (R)-N-(ethoxycarbonyl)-phenylglycinate
• 英文别名: 2-N-ethoxycarbonylamino-2-phenylethanoate；methyl (2R)-2-(ethoxycarbonylamino)-2-phenylacetate
• CAS: 161533-37-5
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: CHGRIMACYWNDSC-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (R)-N-(ethoxycarbonyl)-phenylglycinate 在 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 生成 4(R)-phenyl-5,5-bis(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone
  参考文献：
  名称：

  Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliaries from α-Amino Acids

  摘要：

  A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral a-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.

  DOI：

  10.1021/jo051696n
• 作为产物：
  描述：

  左旋苯甘氨酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 9.0h， 生成 methyl (R)-N-(ethoxycarbonyl)-phenylglycinate
  参考文献：
  名称：

  Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliaries from α-Amino Acids

  摘要：

  A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral a-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.

  DOI：

  10.1021/jo051696n

文献信息

• A Simple and Efficient Procedure for the Preparation of Chiral 2-Oxazolidinones from α-Amino Acids
  作者：Norman Lewis、Alexander McKillop、Richard J. K. Taylor、Robert J. Watson

  DOI：10.1080/00397919508011390

  日期：1995.2

  Abstract A modified procedure for the title transformation is described which avoids: (i) a potentially hazardous borane reduction step, and (ii) the intermediacy of water soluble amino alcohols.

  摘要 描述了标题转化的改进程序，它避免了：(i) 潜在危险的硼烷还原步骤，和 (ii) 水溶性氨基醇的中间体。
• Practical Synthesis of Fluorous Oxazolidinone Chiral Auxiliaries from α-Amino Acids
  作者：Jason E. Hein、Laina M. Geary、Ashley A. Jaworski、Philip G. Hultin

  DOI：10.1021/jo051696n

  日期：2005.11.1

  A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral a-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.