(3R)-3-[(2-chloroacetyl)amino]-3-phenylpropanoic acid | 742100-93-2

• 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: (3R)-3-[(2-chloroacetyl)amino]-3-phenylpropanoic acid
• CAS: 742100-93-2
• 化学式: C₁₁H₁₂ClNO₃
• 分子量: 241.674
• InChiKey: HWOAOBZSOZZKBB-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(2-chloro-acetylamino)-3-phenyl-propionic acid 在 Porcine kidney acylase I 作用下， 反应 48.0h， 以36%的产率得到(S)-3-氨基-3-苯基丙酸
  参考文献：
  名称：

  Development of a Commercial Process for (S)-β-Phenylalanine

  摘要：

  The development of a commercial manufacturing route for (S)-beta-phenylalanine 8, a key pharmaceutical building block, is described. The different approaches which were investigated, based on catalytic asymmetric hydrogenation of enamide intermediates and on biocatalysis using acylase and lipase hydrolyses, are compared. The lipase resolution route was chosen for scale-up, and the final two-step process, based on readily available raw materials, is shown to be robust at full manufacturing scale

  DOI：

  10.1021/op200084g

文献信息

• Development of a Commercial Process for (<i>S</i>)-β-Phenylalanine
  作者：J. Ian Grayson、Jürgen Roos、Steffen Osswald

  DOI：10.1021/op200084g

  日期：2011.9.16

  The development of a commercial manufacturing route for (S)-beta-phenylalanine 8, a key pharmaceutical building block, is described. The different approaches which were investigated, based on catalytic asymmetric hydrogenation of enamide intermediates and on biocatalysis using acylase and lipase hydrolyses, are compared. The lipase resolution route was chosen for scale-up, and the final two-step process, based on readily available raw materials, is shown to be robust at full manufacturing scale