(4S)-3-<(Benzyloxy)carbonyl>-1-methyl-2-oxoimidazolidine-4-carboxylic acid | 168292-63-5

• 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: (4S)-3-<(Benzyloxy)carbonyl>-1-methyl-2-oxoimidazolidine-4-carboxylic acid
• 英文别名: (S)-3-((benzyloxy)carbonyl)-1-methyl-2-oxoimidazolidine-4-carboxylic acid；(4S)-1-methyl-2-oxo-3-phenylmethoxycarbonylimidazolidine-4-carboxylic acid
• CAS: 168292-63-5
• 化学式: C₁₃H₁₄N₂O₅
• 分子量: 278.265
• InChiKey: YONVBUKGFAEQAF-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-3-<(Benzyloxy)carbonyl>-1-methyl-2-oxoimidazolidine-4-carboxylic acid 在 dimethyl sulfide borane 、 硫酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (4S)-3-<(Benzyloxy)carbonyl>-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：

  (4S)-3-苯甲氧羰基-1-甲基-2-氧代咪唑啉-4-羧酸叔丁酯 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以73%的产率得到(4S)-3-<(Benzyloxy)carbonyl>-1-methyl-2-oxoimidazolidine-4-carboxylic acid
  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

文献信息

• Novel 2-oxoimidazolidine derivative, a process for preparing same and a pharmaceutical composition containing the 2-oxoimidazolidine derivative
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：EP0052696A1

  公开（公告）日：1982-06-02

  A 2-oxoimidazolidine derivative of the formula: wherein R1 is lower alkyl or phenyl-lower alkyl and R2 is lower alkyl or phenyl, and a process for preparation thereof are disclosed. Said 2-oxoimidazolidine derivative (I) or a pharmaceutically acceptable salt thereof in form of a pharmaceutical composition exhibits useful hypotensive activity.

  本发明公开了一种式如下的 2-氧代咪唑烷衍生物： 其中 R1 为低级烷基或苯基-低级烷基，R2 为低级烷基或苯基，本发明公开了一种 2-氧代咪唑烷衍生物及其制备方法。所述 2-氧代咪唑烷衍生物 (I) 或其药学上可接受的盐以药物组合物的形式表现出有用的降血压活性。
• 2-Oxo-imidazolidine compounds, a process for preparing the same and a pharmaceutical composition
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：EP0095163A2

  公开（公告）日：1983-11-30

  Novel 2-oxo-imidazolidine derivative of the formula: wherein R1 is lower alkyl or phenyl-lower alkyl, R2 is lower alkyl, R3 is alkyl of one to 12 carbon atoms or phenyl-lower alkyl and R4 is hydrogen or lower alkyl, pharmaceutically acceptable salts thereof and processes for preparing the same are disclosed. In form of pharmaceutical compositions said compounds (I) and salts thereof exhibit hypotensive activity.

  式中的新型 2-氧代咪唑烷衍生物： 其中，R1 是低级烷基或苯基低级烷基，R2 是低级烷基，R3 是 1 至 12 个碳原子的烷基或苯基低级烷基，R4 是氢或低级烷基，公开了其药学上可接受的盐及其制备工艺。以药物组合物的形式，所述化合物 (I) 及其盐类具有降血压活性。
• US4380644A
  申请人：——

  公开号：US4380644A

  公开（公告）日：1983-04-19
• US4508727A
  申请人：——

  公开号：US4508727A

  公开（公告）日：1985-04-02
• 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.