(R)-2-{acetyl-[(S)-1-(4-methoxy-phenyl)-ethyl]-amino}-N-benzyl-3-methoxy-propionamide | 1437318-02-9

• 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: (R)-2-{acetyl-[(S)-1-(4-methoxy-phenyl)-ethyl]-amino}-N-benzyl-3-methoxy-propionamide
• 英文别名: (2R)-2-[acetyl-[(1S)-1-(4-methoxyphenyl)ethyl]amino]-N-benzyl-3-methoxypropanamide
• CAS: 1437318-02-9
• 化学式: C₂₂H₂₈N₂O₄
• 分子量: 384.475
• InChiKey: CGUNDOJCNKEPAU-HRAATJIYSA-N

物化性质

• 熔点：
  128 °C(Solvent: Ethanol ; Water)
• 沸点：
  600.4±55.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-{acetyl-[(S)-1-(4-methoxy-phenyl)-ethyl]-amino}-N-benzyl-3-methoxy-propionamide 在 甲酸 、 苯甲醚 作用下， 反应 1.0h， 以83%的产率得到拉克酰胺
  参考文献：
  名称：

  Development of Scalable Conditions for the Ugi Reaction—Application to the Synthesis of (R)-Lacosamide

  摘要：

  The Ugi reaction is applied for the preparation of (R)-lacosamide, an important drug for the treatment of epilepsy. To this end, key issues associated with the Ugi reaction, such as a practical preparation of the foul-smelling isocyanide as well as the efficient introduction of chirality via a cheap and easily removable chiral directing:group, were solved. Enantiomerically pure (>99.9% ee) drug substance meeting all required purity specifications is prepared in operationally simple four steps, in 40% overall yield from the commodity chemical benzylamine.

  DOI：

  10.1021/acs.oprd.5b00228
• 作为产物：
  描述：

  2-苯乙酰胺 在 吡啶 、 甲基磺酰氯 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 21.5h， 生成 (R)-2-{acetyl-[(S)-1-(4-methoxy-phenyl)-ethyl]-amino}-N-benzyl-3-methoxy-propionamide 、 (S)-2-{acetyl-[(S)-1-(4-methoxy-phenyl)-ethyl]-amino}-N-benzyl-3-methoxy-propionamide
  参考文献：
  名称：

  Development of Scalable Conditions for the Ugi Reaction—Application to the Synthesis of (R)-Lacosamide

  摘要：

  The Ugi reaction is applied for the preparation of (R)-lacosamide, an important drug for the treatment of epilepsy. To this end, key issues associated with the Ugi reaction, such as a practical preparation of the foul-smelling isocyanide as well as the efficient introduction of chirality via a cheap and easily removable chiral directing:group, were solved. Enantiomerically pure (>99.9% ee) drug substance meeting all required purity specifications is prepared in operationally simple four steps, in 40% overall yield from the commodity chemical benzylamine.

  DOI：

  10.1021/acs.oprd.5b00228

文献信息

• [EN] PROCESS FOR THE PRODUCTION OF N-SUBSTITUTED 2-(ACETYLAMINO)-N'-BENZYL-3-METHOXYPROPANAMIDES<br/>[FR] PROCÉDÉ POUR LA PRODUCTION DE 2-(ACÉTYLAMINO)-N'-BENZYL-3-MÉTHOXYPROPANAMIDES N-SUBSTITUÉS
  申请人：SANOFI AVENTIS DEUTSCHLAND

  公开号：WO2013072330A1

  公开（公告）日：2013-05-23

  A process for the production of N-substituted 2-(acetylamino)-N'-benzyl-3-methoxypropanamides and subsequent treatment with acids is described. This process can be used for the production of (R)-Lacosamide.

  描述了一种生产N-取代的2-(乙酰氨基)-N'-苄基-3-甲氧基丙酰胺并随后用酸处理的过程。该过程可用于生产(R)-拉考酰胺。
• PROCESS FOR THE PRODUCTION OF N-SUBSTITUTED 2-(ACETYLAMINO)-N'-BENZYL-3-METHOXYPROPANAMIDES
  申请人：Sanofi-Aventis Deutschland GmbH

  公开号：EP2780318A1

  公开（公告）日：2014-09-24
• EP2780318B1
  申请人：——

  公开号：EP2780318B1

  公开（公告）日：2015-08-26
• Development of Scalable Conditions for the Ugi Reaction—Application to the Synthesis of (<i>R</i>)-Lacosamide
  作者：Hermut Wehlan、Jan Oehme、Alexander Schäfer、Kai Rossen

  DOI：10.1021/acs.oprd.5b00228

  日期：2015.12.18

  The Ugi reaction is applied for the preparation of (R)-lacosamide, an important drug for the treatment of epilepsy. To this end, key issues associated with the Ugi reaction, such as a practical preparation of the foul-smelling isocyanide as well as the efficient introduction of chirality via a cheap and easily removable chiral directing:group, were solved. Enantiomerically pure (>99.9% ee) drug substance meeting all required purity specifications is prepared in operationally simple four steps, in 40% overall yield from the commodity chemical benzylamine.