(5S)-3-(1-(hydroxy)propan-2-yl)-5-(m-tolyloxymethyl)oxazolidin-2-one | 1044739-94-7

• 英文名称: (5S)-3-(1-(hydroxy)propan-2-yl)-5-(m-tolyloxymethyl)oxazolidin-2-one
• CAS: 1044739-94-7
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: GUUCQEJLCORDDO-YUZLPWPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5S)-3-(1-(hydroxy)propan-2-yl)-5-(m-tolyloxymethyl)oxazolidin-2-one 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以65%的产率得到
  参考文献：
  名称：

  Facile Radiosynthesis of Fluorine-18 Labeled β-Blockers. Synthesis, Radiolabeling, and ex Vivo Biodistribution of [¹⁸F]-(2S and 2R)-1-(1-Fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol

  摘要：

  An efficient and genral method has been developed for fluorine-18 labeling of beta-blockers that possess the propanolamine moiety. A new synthetically versatile intermediate, 3-(1-(benzyloxy)propan-2-yl)-2-oxoox-azolidin-5-yl)methyl 4-methylbenzenesulfonate (13), was prepared and can be conjugated to any phenoxy core. To demonstrate the synthetic methodology, fluorinated derivatives of toliprolol were prepared, namely, [(18)F]-(2S and 2R)-]-(1-fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol ((2S and 2R)-[(18)F]1). The radiosyntheses were accomplished in < 1 h, with 20-24% (uncorrected for decay, n = 7) radiochemical yields, > 96% radiochemical and > 99% enantiomeric purities, with specific activities of 0.9-1.1 Ci/mu mol(EOS). Ex vivo biodistribution studies with the radiotracers demonstrated excessively rapid washout that May limit their use for cerebral PET imaging.

  DOI：

  10.1021/jm800227h
• 作为产物：
  描述：

  (5S)-3-(1-(benzyloxy)propan-2-yl)-5-(m-tolyloxymethyl)oxazolidin-2-one 在 palladium dihydroxide 、 10% palladium on charcoal 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到(5S)-3-(1-(hydroxy)propan-2-yl)-5-(m-tolyloxymethyl)oxazolidin-2-one
  参考文献：
  名称：

  Facile Radiosynthesis of Fluorine-18 Labeled β-Blockers. Synthesis, Radiolabeling, and ex Vivo Biodistribution of [¹⁸F]-(2S and 2R)-1-(1-Fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol

  摘要：

  An efficient and genral method has been developed for fluorine-18 labeling of beta-blockers that possess the propanolamine moiety. A new synthetically versatile intermediate, 3-(1-(benzyloxy)propan-2-yl)-2-oxoox-azolidin-5-yl)methyl 4-methylbenzenesulfonate (13), was prepared and can be conjugated to any phenoxy core. To demonstrate the synthetic methodology, fluorinated derivatives of toliprolol were prepared, namely, [(18)F]-(2S and 2R)-]-(1-fluoropropan-2-ylamino)-3-(m-tolyloxy)propan-2-ol ((2S and 2R)-[(18)F]1). The radiosyntheses were accomplished in < 1 h, with 20-24% (uncorrected for decay, n = 7) radiochemical yields, > 96% radiochemical and > 99% enantiomeric purities, with specific activities of 0.9-1.1 Ci/mu mol(EOS). Ex vivo biodistribution studies with the radiotracers demonstrated excessively rapid washout that May limit their use for cerebral PET imaging.

  DOI：

  10.1021/jm800227h