methyl (2R)-2-[(4-chlorobenzoyl)amino]-3-phenylpropanoate

• 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 (2R)-2-[(4-chlorobenzoyl)amino]-3-phenylpropanoate
• 化学式: C₁₇H₁₆ClNO₃
• 分子量: 317.772
• InChiKey: KREXJITYFSDYJS-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲醇 、 4-Benzyl-2-(p-chlor-phenyl)-Δ²-oxazolinon-(5) 以 various solvent(s) 为溶剂， 反应 72.0h， 生成 (S)-methyl (4-chlorobenzoyl)phenylalaninate 、 methyl (2R)-2-[(4-chlorobenzoyl)amino]-3-phenylpropanoate
  参考文献：
  名称：

  Enzymic asymmetric synthesis of .alpha.-amino acids. Enantioselective cleavage of 4-substituted oxazolin-5-ones and thiazolin-5-ones

  摘要：

  A general enzymatic asymmetric synthesis of L-alpha-amino acids has been developed. This method entails the use of the Pseudomonas cepacia lipase (P-30) to catalyze the enantioselective methanolysis of a variety of 4-substituted 2-phenyloxazolin-5-one derivatives in a nonpolar organic solvent to furnish optically-active N-benzoyl-L-alpha-amino acid methyl esters (ee = 66-98%), which in turn is subjected to a protease-catalyzed kinetic resolution yielding enantiomerically-pure N-benzoyl-L-alpha-amino acids. This synergistic coupling of two enzymes allows the ready preparation of L-alpha-amino acids of high enantiopurity in yields greater than 50%, an inherent advantage over conventional resolution procedures. Two proteases were found to catalyze the enantioselective hydrolysis of a variety of 4-substituted 2-phenylthiazolin-5-one derivatives to give N-(thiobenzoyl)-L-alpha-amino acids of high optical purity.

  DOI：

  10.1021/jo00064a010