甲基(2-氨基-1-甲氧基-2-氧代乙基)氨基甲酸酯 | 145275-67-8

• 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
• 中文名称: 甲基(2-氨基-1-甲氧基-2-氧代乙基)氨基甲酸酯
• 英文名称: 2-((Methoxycarbonyl)amino)-2-methoxyacetamide
• 英文别名: methyl N-(2-amino-1-methoxy-2-oxoethyl)carbamate
• CAS: 145275-67-8
• 化学式: C₅H₁₀N₂O₄
• 分子量: 162.145
• InChiKey: GKKAAYNVEGHRKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-双(氯二甲基硅基)乙烷 、 甲基(2-氨基-1-甲氧基-2-氧代乙基)氨基甲酸酯 在 三乙胺 作用下， 以 苯 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  Synthesis of racemic .alpha.-amino carboxamides via Lewis acid-mediated reactions of .alpha.-methoxyglycinamide derivatives with allylsilanes: enzymic resolution to optically active .alpha.-amino acids

  摘要：

  A short and expedient synthetic route to optically active, saturated and gamma,delta-unsaturated alpha-amino acids is reported. The key step is a BF3.OEt2-mediated reaction of allylsilanes with N-(alkoxycarbonyl)-alpha-methoxyglycinamides 11-15, leading to the corresponding gamma,delta-unsaturated alpha-aminocarboxamides. The genuine S(N)1-character of this process with iminium ion 6 as intermediate is proven in the case of the glycine ester 10. Thus, reaction of enzymatically resolved 10 with pi-nucleophiles leads to racemic products. The most useful iminium precursors are the N-methoxyamides 12-14 providing good yields of coupling products. The most convenient N-protective group is the allyloxycarbonyl group. Deprotection proceeds via a Pd(0)-catalyzed transprotection to the corresponding BOC-protected analogues. Four examples of the enzymatic resolution of alpha-amino carboxamides, by using an L-specific aminopeptidase from Pseudomonas putida, are described in detail. Most notably, secondary N-methoxyamides are good substrates for the enzyme to provide the desired a-amino acids in high optical purity.

  DOI：

  10.1021/jo00051a019
• 作为产物：
  描述：

  N-甲氧基羰基-2-甲氧基-DL-甘氨酸甲酯 在 ammonium hydroxide 作用下， 反应 5.0h， 以70%的产率得到甲基(2-氨基-1-甲氧基-2-氧代乙基)氨基甲酸酯
  参考文献：
  名称：

  Synthesis of racemic .alpha.-amino carboxamides via Lewis acid-mediated reactions of .alpha.-methoxyglycinamide derivatives with allylsilanes: enzymic resolution to optically active .alpha.-amino acids

  摘要：

  A short and expedient synthetic route to optically active, saturated and gamma,delta-unsaturated alpha-amino acids is reported. The key step is a BF3.OEt2-mediated reaction of allylsilanes with N-(alkoxycarbonyl)-alpha-methoxyglycinamides 11-15, leading to the corresponding gamma,delta-unsaturated alpha-aminocarboxamides. The genuine S(N)1-character of this process with iminium ion 6 as intermediate is proven in the case of the glycine ester 10. Thus, reaction of enzymatically resolved 10 with pi-nucleophiles leads to racemic products. The most useful iminium precursors are the N-methoxyamides 12-14 providing good yields of coupling products. The most convenient N-protective group is the allyloxycarbonyl group. Deprotection proceeds via a Pd(0)-catalyzed transprotection to the corresponding BOC-protected analogues. Four examples of the enzymatic resolution of alpha-amino carboxamides, by using an L-specific aminopeptidase from Pseudomonas putida, are described in detail. Most notably, secondary N-methoxyamides are good substrates for the enzyme to provide the desired a-amino acids in high optical purity.

  DOI：

  10.1021/jo00051a019

文献信息

• Synthesis of racemic .alpha.-amino carboxamides via Lewis acid-mediated reactions of .alpha.-methoxyglycinamide derivatives with allylsilanes: enzymic resolution to optically active .alpha.-amino acids
  作者：Eric C. Roos、Hendrik H. Mooiweer、Henk Hiemstra、W. Nico Speckamp、Bernard Kaptein、Wilhelmus H. J. Boesten、Johan Kamphuis

  DOI：10.1021/jo00051a019

  日期：1992.12

  A short and expedient synthetic route to optically active, saturated and gamma,delta-unsaturated alpha-amino acids is reported. The key step is a BF3.OEt2-mediated reaction of allylsilanes with N-(alkoxycarbonyl)-alpha-methoxyglycinamides 11-15, leading to the corresponding gamma,delta-unsaturated alpha-aminocarboxamides. The genuine S(N)1-character of this process with iminium ion 6 as intermediate is proven in the case of the glycine ester 10. Thus, reaction of enzymatically resolved 10 with pi-nucleophiles leads to racemic products. The most useful iminium precursors are the N-methoxyamides 12-14 providing good yields of coupling products. The most convenient N-protective group is the allyloxycarbonyl group. Deprotection proceeds via a Pd(0)-catalyzed transprotection to the corresponding BOC-protected analogues. Four examples of the enzymatic resolution of alpha-amino carboxamides, by using an L-specific aminopeptidase from Pseudomonas putida, are described in detail. Most notably, secondary N-methoxyamides are good substrates for the enzyme to provide the desired a-amino acids in high optical purity.