(RS)-5-trimethylammoniomethyl-2-oxazolidinone chloride | 166395-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (RS)-5-trimethylammoniomethyl-2-oxazolidinone chloride
• 英文别名: Trimethyl-[(2-oxo-1,3-oxazolidin-5-yl)methyl]azanium;chloride
• CAS: 166395-17-1
• 化学式: C₇H₁₅N₂O₂*Cl
• 分子量: 194.661
• InChiKey: CBOAVIPSVIISIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.19
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  左卡尼汀杂质C 在 三氯异氰尿酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 51.17h， 生成 (RS)-5-trimethylammoniomethyl-2-oxazolidinone chloride
  参考文献：
  名称：

  From carnitinamide to 5-aminomethyl-2-oxazolidinones

  摘要：

  Carnitinamide chloride, an immediate synthetic precursor of carnitine, was chlorinated at the amide nitrogen. The resultant carnitinechloramide chloride, when treated with a base, revealed that the first-formed isolable and characterisable carnitinechloramide inner salt undergoes solid state conversion into 5-trimethylammoniomethyl-2-oxazolidinone chloride via Hoffmann rearrangement and intramolecular cyclization of the beta-hydroxyisocyanate. The trimethylaminomethyl substituent at C-5 of the 2-oxazolidinone was converted into a dimethylaminomethyl group by microwave-assisted demethylation in DMF and then into a methylaminomethyl group by decomposition of the alpha-chloroethyl carbamate obtained by treatment with alpha-chloroethyl chloroformate. This sequence of reactions was then applied to both (S)- and (R)-carnitinamide chloride without any racemization to yield both enantiomers of 5-aminomethyl-2-oxazolidinones that are mono-, di- and tri-methylated at the exocyclic nitrogen. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.02.006