(S)-4-(2-Methoxycarbonyl-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester | 57355-89-2

• 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)-4-(2-Methoxycarbonyl-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester
• 英文别名: benzyl (4S)-4-(3-methoxy-3-oxopropyl)-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 57355-89-2
• 化学式: C₁₅H₁₇NO₆
• 分子量: 307.303
• InChiKey: HEDONMMVUXJFFP-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-(2-Methoxycarbonyl-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 在 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-5-Hydroxy-4-(2-methoxycarbonyl-ethyl)-5-trifluoromethyl-oxazolidine-3-carboxylic acid benzyl ester
  参考文献：
  名称：

  Reaction of ruppert’s reagent (TMS-CF3) with Oxazolidinones: Synthesis of protected α-amino trifluoromethylketones

  摘要：

  (Trifluoromethyl)trimethylsilane adds to alpha-amino acid derived oxazolidin-5-ones in excellent yields. The adducts can be converted into protected alpha-amino trifluoromethylketones by acid hydrolysis.

  DOI：

  10.1016/0040-4039(95)01619-s
• 作为产物：
  描述：

  重氮甲烷 、 (S)-(+)-3-(苄氧基羰基)-5-氧代-4-噁唑啉丙酸 以 乙酸乙酯 为溶剂， 反应 0.42h， 以97%的产率得到(S)-4-(2-Methoxycarbonyl-ethyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester
  参考文献：
  名称：

  Reaction of (Trifluoromethyl)trimethylsilane with Oxazolidin-5-ones:  Synthesis of Peptidic and Nonpeptidic Trifluoromethyl Ketones

  摘要：

  (Trifluoromethyl)trimethylsilane (TMS-CF3, the Ruppert Reagent) reacts with a variety of amino acid derived N-substituted oxazolidin-5-ones in excellent yields. Mild acid hydrolysis of adducts with electron-releasing substituents at C-2 affords N-substituted cx-amino trifluoromethyl ketones (TFMKs). N-CBZ-protected alpha-amino TFMKs are converted into hitherto unreported hydrochloride salts of alpha-amino TFMKs by hydrogenolysis. Coupling with aminoacid fluorides gives access to peptidic TFMKs which are of utility as protease inhibitors.

  DOI：

  10.1021/jo980443+

文献信息

• Cleavage of benzyloxycarbonyl-5-oxazolidinones to α-benzyloxycarbonylamino-α-alkyl esters by alcohols and sodium hydrogen carbonate
  作者：Pietro Allevi、Giuliana Cighetti、Mario Anastasia

  DOI：10.1016/s0040-4039(01)00971-6

  日期：2001.7

  The reaction of benzyloxycarbonyl-5-oxazolidinones with alcohols and sodium hydrogen carbonate to afford the corresponding benzyloxycarbonyl esters is described.

  描述了苄氧羰基-5-恶唑烷酮与醇和碳酸氢钠的反应，得到相应的苄氧羰基酯。
• US6043278A
  申请人：——

  公开号：US6043278A

  公开（公告）日：2000-03-28
• Reaction of (Trifluoromethyl)trimethylsilane with Oxazolidin-5-ones:  Synthesis of Peptidic and Nonpeptidic Trifluoromethyl Ketones
  作者：Magnus W. Walter、Robert M. Adlington、Jack E. Baldwin、Christopher J. Schofield

  DOI：10.1021/jo980443+

  日期：1998.7.1

  (Trifluoromethyl)trimethylsilane (TMS-CF3, the Ruppert Reagent) reacts with a variety of amino acid derived N-substituted oxazolidin-5-ones in excellent yields. Mild acid hydrolysis of adducts with electron-releasing substituents at C-2 affords N-substituted cx-amino trifluoromethyl ketones (TFMKs). N-CBZ-protected alpha-amino TFMKs are converted into hitherto unreported hydrochloride salts of alpha-amino TFMKs by hydrogenolysis. Coupling with aminoacid fluorides gives access to peptidic TFMKs which are of utility as protease inhibitors.
• Reaction of ruppert’s reagent (TMS-CF3) with Oxazolidinones: Synthesis of protected α-amino trifluoromethylketones
  作者：Magnus W. Walter、Robert M. Adlington、Jack E. Baldwin、John Chuhan、Christopher J. Schofield

  DOI：10.1016/0040-4039(95)01619-s

  日期：1995.10

  (Trifluoromethyl)trimethylsilane adds to alpha-amino acid derived oxazolidin-5-ones in excellent yields. The adducts can be converted into protected alpha-amino trifluoromethylketones by acid hydrolysis.