(5R)-3-aminomethyl-5-methyloctanoic acid | 942219-71-8

• 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: (5R)-3-aminomethyl-5-methyloctanoic acid
• 英文别名: (5R)-3-(aminomethyl)-5-methyloctanoic acid
• CAS: 942219-71-8
• 化学式: C₁₀H₂₁NO₂
• 分子量: 187.282
• InChiKey: KKXFMWXZXDUYBF-VEDVMXKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R)-3-aminomethyl-5-methyloctanoic acid 在 (S)-(+)-扁桃酸 作用下， 以 乙醇 、 水 为溶剂， 以17 kg的产率得到(3S,5R)-3-aminomethyl-5-methyl-octanoic acid
  参考文献：
  名称：

  Chemical Development of an α2δ Ligand, (3S,5R)-3-(Aminomethyl)-5-methyloctanoic Acid

  摘要：

  Three synthetic approaches, suitable for the large scale manufacture of the alpha 2 delta-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocente was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.

  DOI：

  10.1021/op2001832
• 作为产物：
  描述：

  (5R)-3-cyano-5-methyloctanoic acid ethyl ester 在 水 、 sodium hydroxide 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 乙醇 为溶剂， 70.0 ℃ 、344.75 kPa 条件下， 反应 2.0h， 以76 kg的产率得到(5R)-3-aminomethyl-5-methyloctanoic acid
  参考文献：
  名称：

  Chemical Development of an α2δ Ligand, (3S,5R)-3-(Aminomethyl)-5-methyloctanoic Acid

  摘要：

  Three synthetic approaches, suitable for the large scale manufacture of the alpha 2 delta-ligand, (3S,5R)-3-(aminomethyl)-5-methyloctanoic acid 3, have been evaluated. The selected seven step manufacturing process has then been optimized and used to deliver over 20 kg of API; salient features of the synthesis include the use of 4,4,4-trimethoxybutyronitrile as an efficient four carbon amino acid equivalent. Highly selective kinetic resolution of the C3 stereocente was accomplished via diastereoselective hydrolysis of a cyanoester intermediate using Amano Lipase PS-SD. Extensive process optimisation of the route starting from (R)-2-methylpentanol, led to significant improvements through telescoping, with less than 62 kg of solvent being needed to produce 1 kg of API.

  DOI：

  10.1021/op2001832

文献信息

• Preparation of gamma-amino acids having affinity for the alpha-2-delta protein
  申请人：Evans Claire Margaret

  公开号：US20070141684A1

  公开（公告）日：2007-06-21

  Disclosed are materials and methods for preparing optically active γ-amino acids of Formula 1, which bind to the alpha-2-delta (α2δ) subunit of a calcium channel.

  本发明公开了一种制备光学活性γ-氨基酸的材料和方法，其化合物符合公式1，可以与钙通道的α2δ亚单位结合。
• Preparation of Gamma-Amino Acids Having Affinity for The Alpha-2-Delta Protein
  申请人：Evans Margaret Claire

  公开号：US20090299093A1

  公开（公告）日：2009-12-03

  Disclosed are materials and methods for preparing optically active γ-amino acids of Formula 1, which bind to the alpha-2-delta (α2δ) subunit of a calcium channel.

  本发明涉及一种制备结合到钙通道的α2δ亚基的光学活性γ-氨基酸的材料和方法，其化学式为1。
• PREPARATION OF GAMMA-AMINO ACIDS HAVING AFFINITY FOR THE ALPHA-2-DELTA PROTEIN
  申请人：Pfizer Products Inc.

  公开号：EP1973867A1

  公开（公告）日：2008-10-01
• COMBINATION THERAPY OF LOWER URINARY TRACT DISORDERS WITH 2 LIGANDS AND NSAIDS
  申请人：Recordati Ireland Limited

  公开号：EP2125021A1

  公开（公告）日：2009-12-02
• COMBINATION THERAPY OF LOWER URINARY TRACT DISORDERS WITH ALPHA 2DELTA LIGANDS AND NSAIDS
  申请人：Recordati Ireland Limited

  公开号：EP2125021B8

  公开（公告）日：2012-02-15