benzyl (S)-5-(hydroxymethyl)-3-methyl-2-oxoimidazolidine-1-carboxylate | 90157-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (S)-5-(hydroxymethyl)-3-methyl-2-oxoimidazolidine-1-carboxylate
• 英文别名: benzyl (5S)-5-(hydroxymethyl)-3-methyl-2-oxoimidazolidine-1-carboxylate
• CAS: 90157-23-6
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: GBHQGSHJDNMPGU-NSHDSACASA-N

物化性质

• 沸点：
  406.2±47.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (S)-5-(hydroxymethyl)-3-methyl-2-oxoimidazolidine-1-carboxylate 在 palladium on activated charcoal 硫酸 、 potassium tert-butylate 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 17.83h， 生成 (4S)-3-<(2S)-2-(N-Benzylamino)propionyl>-4-(tert-butoxymethyl)-1-methyl-2-oxoimidazolidine
  参考文献：
  名称：

  Stereospecific Amination by Dynamic Kinetic Resolution Utilizing 2-Oxoimidazolidine-4-carboxylate as a Novel Chiral Auxiliary

  摘要：

  A novel type of stereospecific amination by dynamic kinetic resolution using (4S)-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. A reaction of a diastereomeric mixture of (4S)-3-[(2RS)-2-bromoacyl]-2-oxoimidazolidine-4-carboxylates 4 with an amine in the presence of a base in HMPA predominantly afforded (4S)-3-[(2R)-2-(alkylamino)acyl]-2-oxoimidazolidine-4-carboxylates (S,R)-7 in good yields. The reaction proceeded by stereospecific S(N)2 type amination incorporated with rapid interconversion between the substrates (S,S)-4 and (S,R)-4. Mechanistic study suggested that the unique stereoselectivity was induced through the interaction between an amine and the ester group of (S,S)-4 in the transition state. The chiral auxiliary was easily removed with alkoxide anion to afford the alpha-amino acid synthon in good yields.

  DOI：

  10.1021/jo00126a029
• 作为产物：
  描述：

  methyl 3-benzyloxycarbonyl-2-oxo-imidazolidine-4(S)-carboxylate 在 sodium tetrahydroborate 、 乙醇 、 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 23.0h， 生成 benzyl (S)-5-(hydroxymethyl)-3-methyl-2-oxoimidazolidine-1-carboxylate
  参考文献：
  名称：

  Bicyclic-Fused Heteroaryl or Aryl Compounds

  摘要：

  所述化合物的异构体和药学上可接受的盐已被披露，其中所述化合物具有如规范中定义的Ia式结构。相应的药物组合物、治疗方法、合成方法和中间体也已被披露。

  公开号：

  US20150284405A1

文献信息

• Bicyclic-Fused Heteroaryl or Aryl Compounds
  申请人：Pfizer Inc.

  公开号：US20150284405A1

  公开（公告）日：2015-10-08

  Compounds, tautomers and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula Ia, as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  所述化合物的异构体和药学上可接受的盐已被披露，其中所述化合物具有如规范中定义的Ia式结构。相应的药物组合物、治疗方法、合成方法和中间体也已被披露。
• Stereospecific Amination by Dynamic Kinetic Resolution Utilizing 2-Oxoimidazolidine-4-carboxylate as a Novel Chiral Auxiliary
  作者：Hitoshi Kubota、Akira Kubo、Masami Takahashi、Ryo Shimizu、Tadamasa Da-te、Kimio Okamura、Ken-ichi Nunami

  DOI：10.1021/jo00126a029

  日期：1995.10

  A novel type of stereospecific amination by dynamic kinetic resolution using (4S)-2-oxoimidazolidine-4-carboxylate (1) as a chiral auxiliary was developed. A reaction of a diastereomeric mixture of (4S)-3-[(2RS)-2-bromoacyl]-2-oxoimidazolidine-4-carboxylates 4 with an amine in the presence of a base in HMPA predominantly afforded (4S)-3-[(2R)-2-(alkylamino)acyl]-2-oxoimidazolidine-4-carboxylates (S,R)-7 in good yields. The reaction proceeded by stereospecific S(N)2 type amination incorporated with rapid interconversion between the substrates (S,S)-4 and (S,R)-4. Mechanistic study suggested that the unique stereoselectivity was induced through the interaction between an amine and the ester group of (S,S)-4 in the transition state. The chiral auxiliary was easily removed with alkoxide anion to afford the alpha-amino acid synthon in good yields.