methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate | 1253091-76-7

• 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 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate
• 英文别名: N-Boc-(RS)-2-chlorophenylglycine methyl ester；Methyl 2-{[(tert-butoxy)carbonyl]amino}-2-(2-chlorophenyl)acetate；methyl 2-(2-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 1253091-76-7
• 化学式: C₁₄H₁₈ClNO₄
• 分子量: 299.754
• InChiKey: LCOQLKXOKYSBQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate 在 protease from Bacillus licheniformis 作用下， 反应 12.0h， 生成 (S)-(+)-2-氯苯甘氨酸甲酯 、 (R)-(-)-2-氯苯基甘氨酸甲脂
  参考文献：
  名称：

  Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel

  摘要：

  The (S)-2-chlorophenylglycine moiety is well recognized in the structure of (S)-clopidogrel, a known antithrombotic drug. We prepared an enantiomerically pure chiral building block via an enzyme-catalyzed resolution of (RS)-N-Boc-2-chlorophenylglycine methylester. The best results were obtained by means of an immobilized subtilisin, the cross-linked enzyme aggregate (Alcalase-CLEA (R)). The high enantiomeric excess of the synthon obtained remained the same over the course of clopidogrel synthesis; the simplicity of the process makes this pathway suitable for large-scale preparation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.040
• 作为产物：
  描述：

  (+/-)-2-氯苯基甘氨酸甲酯盐酸盐 、 tert-butyl (3-cyano-4,6-dimethylpyridin-2-yl) carbonate 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 1.0h， 以95%的产率得到methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate
  参考文献：
  名称：

  tert-Butyl(3-cyano-4,6-dimethylpyridin-2-yl)carbonate as a green and chemoselective N-tert-butoxycarbonylation reagent

  摘要：

  使用tert-丁基(3-氰基-4,6-二甲基吡啶-2基)碳酸酯作为芳香族和脂肪族胺的化学选择性tert-丁氧羰基化试剂已经得到证明（30个示例）。

  DOI：

  10.1039/c9nj00885c

文献信息

• <i>tert</i>-Butyl(3-cyano-4,6-dimethylpyridin-2-yl)carbonate as a green and chemoselective <i>N-tert</i>-butoxycarbonylation reagent
  作者：Fangyu Du、Qifan Zhou、Yang Fu、Hanqi Zhao、Yuanguang Chen、Guoliang Chen

  DOI：10.1039/c9nj00885c

  日期：——

  The use of tert-butyl(3-cyano-4,6-dimethylpyridin-2yl) carbonate as a chemoselective tert-butoxycarbonylation reagent for aromatic and aliphatic amines has been demonstrated (30 examples).

  使用tert-丁基(3-氰基-4,6-二甲基吡啶-2基)碳酸酯作为芳香族和脂肪族胺的化学选择性tert-丁氧羰基化试剂已经得到证明（30个示例）。
• Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel
  作者：Patrizia Ferraboschi、Maria De Mieri、Fiorella Galimberti

  DOI：10.1016/j.tetasy.2010.06.040

  日期：2010.9

  The (S)-2-chlorophenylglycine moiety is well recognized in the structure of (S)-clopidogrel, a known antithrombotic drug. We prepared an enantiomerically pure chiral building block via an enzyme-catalyzed resolution of (RS)-N-Boc-2-chlorophenylglycine methylester. The best results were obtained by means of an immobilized subtilisin, the cross-linked enzyme aggregate (Alcalase-CLEA (R)). The high enantiomeric excess of the synthon obtained remained the same over the course of clopidogrel synthesis; the simplicity of the process makes this pathway suitable for large-scale preparation. (C) 2010 Elsevier Ltd. All rights reserved.