benzyl (D,L)-(3-methyl-1-oxo-1-(phenylamino)butan-2-yl)carbamate

• 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: benzyl (D,L)-(3-methyl-1-oxo-1-(phenylamino)butan-2-yl)carbamate
• 英文别名: Benzyl [3-methyl-1-oxo-1-(phenylamino)butan-2-yl]carbamate；benzyl N-(1-anilino-3-methyl-1-oxobutan-2-yl)carbamate
• 化学式: C₁₉H₂₂N₂O₃
• 分子量: 326.395
• InChiKey: FNZWOLATMXPENQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.263
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (D,L)-(3-methyl-1-oxo-1-(phenylamino)butan-2-yl)carbamate 在 CHIRALCEL OD-H 作用下， 以 正己烷 、 异丙醇 为溶剂， 生成 (S)-N-(benzyloxycarbonyl)valinanilide 、 benzyl (R)-(3-methyl-1-oxo-1-(phenylamino)butan-2-yl)carbamate
  参考文献：
  名称：

  Fast Amide Couplings in Water: Extraction, Column Chromatography, and Crystallization Not Required

  摘要：

  In the micelle of PS-750-M, the presence of 3 degrees amides from the surfactant proline linker mimics dimethylforma-mide, dimethylacetamide, and N-methyl-2-pyrrolidone. The resultant micellar properties enable extremely fast amide couplings mediated by 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (without hydroxybenzotriazole), rather than expensive and specialized coupling agents. Conditions have been developed wherein products precipitate, and isolation by filtration completely avoids the use of organic solvent. This methodology is scalable and avoids product epimerization.

  DOI：

  10.1021/acs.orglett.0c01676

文献信息

• Fast Amide Couplings in Water: Extraction, Column Chromatography, and Crystallization Not Required
  作者：Sudripet Sharma、Nicklas W. Buchbinder、Wilfried M. Braje、Sachin Handa

  DOI：10.1021/acs.orglett.0c01676

  日期：2020.8.7

  In the micelle of PS-750-M, the presence of 3 degrees amides from the surfactant proline linker mimics dimethylforma-mide, dimethylacetamide, and N-methyl-2-pyrrolidone. The resultant micellar properties enable extremely fast amide couplings mediated by 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (without hydroxybenzotriazole), rather than expensive and specialized coupling agents. Conditions have been developed wherein products precipitate, and isolation by filtration completely avoids the use of organic solvent. This methodology is scalable and avoids product epimerization.