(2S,6R)-4-[4-((S)-5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-2,6-dimethyl-piperazine-1-carboxylic acid tert-butyl ester | 866539-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2S,6R)-4-[4-((S)-5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-2,6-dimethyl-piperazine-1-carboxylic acid tert-butyl ester
• CAS: 866539-15-3
• 化学式: C₂₁H₃₁FN₄O₄
• 分子量: 422.5
• InChiKey: KKBJLXAQFGIVOX-LZWOXQAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  88.34
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,6R)-4-[4-((S)-5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-2,6-dimethyl-piperazine-1-carboxylic acid tert-butyl ester 在 TEA 、 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-((S)-3-{4-[(3R,5S)-3,5-Dimethyl-4-(5-nitro-furan-2-ylmethyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide
  参考文献：
  名称：

  Synthesis and SAR of novel oxazolidinones: Discovery of ranbezolid

  摘要：

  Novel oxazolidinones were synthesized containing a number of substituted five-membered heterocycles attached to the 'piperazinyl-phenyl-oxazolidinone' core of eperezolid. Further, the piperazine ring of the core was replaced by other diamino-heterocycles. These modifications led to several compounds with potent activity against a spectrum of resistant and susceptible Gram-positive organisms, along with the identification of ranbezolid (RBx 7644) as a clinical candidate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.063
• 作为产物：
  描述：

  (2R,6S)-4-(2-Fluoro-4-nitro-phenyl)-2,6-dimethyl-piperazine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 正丁基锂 、 sodium azide 、 TEA 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~80.0 ℃ 、379.21 kPa 条件下， 反应 1.5h， 生成 (2S,6R)-4-[4-((S)-5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-2,6-dimethyl-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and SAR of novel oxazolidinones: Discovery of ranbezolid

  摘要：

  Novel oxazolidinones were synthesized containing a number of substituted five-membered heterocycles attached to the 'piperazinyl-phenyl-oxazolidinone' core of eperezolid. Further, the piperazine ring of the core was replaced by other diamino-heterocycles. These modifications led to several compounds with potent activity against a spectrum of resistant and susceptible Gram-positive organisms, along with the identification of ranbezolid (RBx 7644) as a clinical candidate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.063