N-acetyl-2-methylserine methyl ester | 1263775-11-6

• 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: N-acetyl-2-methylserine methyl ester
• 英文别名: methyl (2S)-2-acetamido-3-hydroxy-2-methylpropanoate
• CAS: 1263775-11-6
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: WNMFCAWAEGLFIE-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (S)-2-methylserine methyl ester (1S)-(+)-camphor-10-sulfonate 、 乙酸酐 在 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 20.51h， 生成 N-acetyl-2-methylserine methyl ester 、 N,O-diacetyl-2-methylserine methyl ester 、 N-tert-butoxycarbonyl-O-acetyl-2-methylserine methyl ester 、 N,O-di-tert-butoxycarbonyl-2-methylserine methyl ester 、 (S)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxypropanoic acid methyl ester
  参考文献：
  名称：

  Complementary Syntheses of N,O-Protected-(S)-2-methylserine on a Multikilogram Scale

  摘要：

  Two complementary and scalable approaches have been used to manufacture multikilogram quantities of N,O-protected-(S)-2-methylserine. The first approach uses a diastereomeric salt resolution of 2-methylserine methyl ester as the (1S)-(+)-camphorsulfonate salt, and was used to rapidly access 15 kg of (S)-3-tert-butoxycarbonyl-2,2,4-trimethyl-1,3-oxazolidine-4-carboxylic acid with > 99% ee. The second approach involves a stereoselective enolate methylation of a chiral cyclic L-serine derivative under cryogenic conditions. The four-step telescoped process, starting from L-serine methyl ester, was used to manufacture 20 kg of (2R,4S)-2-tert-butyl-3-tert-butoxycarbonyl-4-methyl-1,3-oxazolidine-4-carboxylic acid in 52% overall yield and 98% ee. The advantages and disadvantages for scale-up of both approaches are discussed.

  DOI：

  10.1021/op100299d

文献信息

• Complementary Syntheses of <i>N</i>,<i>O</i>-Protected-(<i>S</i>)-2-methylserine on a Multikilogram Scale
  作者：Michael S. Anson、Hugh F. Clark、Paul Evans、Martin E. Fox、Jonathan P. Graham、Natalie N. Griffiths、Graham Meek、James A. Ramsden、Alastair J. Roberts、Shaun Simmonds、Matthew D. Walker、Matthew Willets

  DOI：10.1021/op100299d

  日期：2011.3.18

  Two complementary and scalable approaches have been used to manufacture multikilogram quantities of N,O-protected-(S)-2-methylserine. The first approach uses a diastereomeric salt resolution of 2-methylserine methyl ester as the (1S)-(+)-camphorsulfonate salt, and was used to rapidly access 15 kg of (S)-3-tert-butoxycarbonyl-2,2,4-trimethyl-1,3-oxazolidine-4-carboxylic acid with > 99% ee. The second approach involves a stereoselective enolate methylation of a chiral cyclic L-serine derivative under cryogenic conditions. The four-step telescoped process, starting from L-serine methyl ester, was used to manufacture 20 kg of (2R,4S)-2-tert-butyl-3-tert-butoxycarbonyl-4-methyl-1,3-oxazolidine-4-carboxylic acid in 52% overall yield and 98% ee. The advantages and disadvantages for scale-up of both approaches are discussed.