2-[(R)-2-((S)-5-tert-Butoxycarbonyl-3-methyl-2-oxo-imidazolidin-1-yl)-1-methyl-2-oxo-ethyl]-malonic acid | 195828-92-3

• 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: 2-[(R)-2-((S)-5-tert-Butoxycarbonyl-3-methyl-2-oxo-imidazolidin-1-yl)-1-methyl-2-oxo-ethyl]-malonic acid
• 英文别名: 2-[(2R)-1-[(5S)-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-2-oxoimidazolidin-1-yl]-1-oxopropan-2-yl]propanedioic acid
• CAS: 195828-92-3
• 化学式: C₁₅H₂₂N₂O₈
• 分子量: 358.348
• InChiKey: ZVOMCRBHKPFXPH-SFYZADRCSA-N

物化性质

• 沸点：
  522.5±60.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[(R)-2-((S)-5-tert-Butoxycarbonyl-3-methyl-2-oxo-imidazolidin-1-yl)-1-methyl-2-oxo-ethyl]-malonic acid 在 二苯基磷酸 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 生成 (S)-3-((R)-3-Benzyloxycarbonylamino-2-methyl-propionyl)-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Dynamic Kinetic Resolution Utilizing 2-Oxoimidazolidine-4-carboxylate as a Chiral Auxiliary:  Stereoselective Alkylation of α-Bromo Amides with Malonic Ester Enolates

  摘要：

  Stereoselective carbon-carbon bond formation by dynamic kinetic resolution using tert-butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. Reaction of a diastereomeric mixture of tert-butyl (4S)-3-[(2RS)-2-bromoacyl]-1-methyl-2-oxoimidazolidine-4-carboxylates (2) with a malonic ester enolate in HMPA predominantly afforded tert-butyl (4S)-3-[(2R)-2-alkyl-3,3-bis(alkoxycarbonyl)propionyl]-1-methyl-2-oximidazolidine-4-carboxylate [(S,R)-8] in good yields. The stereoselectivity of this reaction was in accordance with our working hypothesis based on the conformational analysis of 2 and elucidated the unique characteristics of 1 as a novel chiral auxiliary for dynamic kinetic resolution. The alkylated products (S,R)-8ej,k were easily converted to chiral cx-alkyl succinic acid derivatives and chiral beta-amino acid derivatives, both of which have been known as key building blocks for the syntheses of a variety of biologically active compounds.

  DOI：

  10.1021/jo970484q
• 作为产物：
  描述：

  dibenzyl 2-[(2R)-1-[(5S)-3-methyl-5-[(2-methylpropan-2-yl)oxycarbonyl]-2-oxoimidazolidin-1-yl]-1-oxopropan-2-yl]propanedioate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以97%的产率得到2-[(R)-2-((S)-5-tert-Butoxycarbonyl-3-methyl-2-oxo-imidazolidin-1-yl)-1-methyl-2-oxo-ethyl]-malonic acid
  参考文献：
  名称：

  Dynamic Kinetic Resolution Utilizing 2-Oxoimidazolidine-4-carboxylate as a Chiral Auxiliary:  Stereoselective Alkylation of α-Bromo Amides with Malonic Ester Enolates

  摘要：

  Stereoselective carbon-carbon bond formation by dynamic kinetic resolution using tert-butyl (4S)-1-methyl-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. Reaction of a diastereomeric mixture of tert-butyl (4S)-3-[(2RS)-2-bromoacyl]-1-methyl-2-oxoimidazolidine-4-carboxylates (2) with a malonic ester enolate in HMPA predominantly afforded tert-butyl (4S)-3-[(2R)-2-alkyl-3,3-bis(alkoxycarbonyl)propionyl]-1-methyl-2-oximidazolidine-4-carboxylate [(S,R)-8] in good yields. The stereoselectivity of this reaction was in accordance with our working hypothesis based on the conformational analysis of 2 and elucidated the unique characteristics of 1 as a novel chiral auxiliary for dynamic kinetic resolution. The alkylated products (S,R)-8ej,k were easily converted to chiral cx-alkyl succinic acid derivatives and chiral beta-amino acid derivatives, both of which have been known as key building blocks for the syntheses of a variety of biologically active compounds.

  DOI：

  10.1021/jo970484q