Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester | 392660-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester
• CAS: 392660-03-6
• 化学式: C₂₂H₃₀FN₃O₇S
• 分子量: 499.561
• InChiKey: JBDIJDBARRQLER-JEWRLFTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105.69
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester 在 palladium on activated charcoal sodium azide 、 TEA 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、379.21 kPa 条件下， 生成 N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-(N-methyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-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：

  [(1α,5α,6α)-3-(2-fluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester 在 palladium on activated charcoal 正丁基锂 、 TEA 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、379.21 kPa 条件下， 反应 1.5h， 生成 Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl 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