(S)-3-((R)-3-tert-Butoxycarbonyl-2-methyl-propionyl)-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester | 195829-02-8

• 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
• 英文名称: (S)-3-((R)-3-tert-Butoxycarbonyl-2-methyl-propionyl)-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-1-methyl-3-[(2R)-2-methyl-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]-2-oxoimidazolidine-4-carboxylate
• CAS: 195829-02-8
• 化学式: C₁₈H₃₀N₂O₆
• 分子量: 370.446
• InChiKey: BPXSOJXQUUIEOO-NEPJUHHUSA-N

物化性质

• 沸点：
  441.9±55.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-((R)-3-tert-Butoxycarbonyl-2-methyl-propionyl)-1-methyl-2-oxo-imidazolidine-4-carboxylic acid tert-butyl ester 在 lithium hydroxide 、 二苯基磷酸 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 生成 tert-butyl (3R)-N-(benzyloxycarbonyl)-3-aminobutanoate
  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 硫酸 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 (S)-3-((R)-3-tert-Butoxycarbonyl-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