(R)-2-[acetyl-((S)-1-naphthalen-2-yl-ethyl)-amino]-N-benzyl-3-methoxy-propionamide | 1437318-07-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2-[acetyl-((S)-1-naphthalen-2-yl-ethyl)-amino]-N-benzyl-3-methoxy-propionamide
• 英文别名: (2R)-2-[acetyl-[(1S)-1-naphthalen-2-ylethyl]amino]-N-benzyl-3-methoxypropanamide
• CAS: 1437318-07-4
• 化学式: C₂₅H₂₈N₂O₃
• 分子量: 404.509
• InChiKey: ZPHVTTAABNMOSC-MHECFPHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯乙酰胺 在 吡啶 、 甲基磺酰氯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 (R)-2-[acetyl-((S)-1-naphthalen-2-yl-ethyl)-amino]-N-benzyl-3-methoxy-propionamide 、 (S)-2-[acetyl-((S)-1-naphthalen-2-yl-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.