3-{[((5R)-3-{4-[(acetyloxyamino)(imino)methyl]phenyl}-4,5-dihydro-5-isoxazolyl)acetyl]amino}-N-(4-benzyloxybutoxycarbonyl)-L-alanine | 752235-81-7

• 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: 3-{[((5R)-3-{4-[(acetyloxyamino)(imino)methyl]phenyl}-4,5-dihydro-5-isoxazolyl)acetyl]amino}-N-(4-benzyloxybutoxycarbonyl)-L-alanine
• 英文别名: (2S)-3-[[2-[(5R)-3-[4-[(Z)-N'-acetyloxycarbamimidoyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]acetyl]amino]-2-(4-phenylmethoxybutoxycarbonylamino)propanoic acid
• CAS: 752235-81-7
• 化学式: C₂₉H₃₅N₅O₉
• 分子量: 597.625
• InChiKey: VBEHKMIFWNWPIW-NOZRDPDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  197.73
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 3-{[((5R)-3-{4-[(acetyloxyamino)(imino)methyl]phenyl}-4,5-dihydro-5-isoxazolyl)acetyl]amino}-N-(4-benzyloxybutoxycarbonyl)-L-alanine 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 20.0 ℃ 、34.47 kPa 条件下， 反应 27.5h， 以40%的产率得到3-{[((5R)-3-{4-[amino(imino)methyl]phenyl}-4,5-dihydro-5-isoxazolyl)acetyl]amino}-N-(4-hydroxybutoxycarbonyl)-L-alanine trifluoroacetate
  参考文献：
  名称：

  Synthesis of N-Butyl Side Chain Hydroxylated Metabolites of Roxifiban, a Platelet Glycoprotein IIb/IIIa Receptor Antagonist

  摘要：

  Syntheses of three n-butyl side chain hydroxylated metabolites of Roxifiban (5, 6a and 6b) are reported. Initial use of benzyl as hydroxyl protecting group gave poor yield during its removal by catalytic hydrogenation, due to complication from N-O cleavage of the isoxazoline. This problem was eliminated by the use of TBDMS as the hydroxyl protecting group. The chemical structures of these metabolites as well as the intermediates have been fully characterized.

  DOI：

  10.3987/com-04-10087
• 作为产物：
  描述：

  tert-butyl N-(benzyloxycarbonyl)-3-({[(5R)-3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetyl}amino)-L-alaninate 在 palladium dihydroxide 吡啶 、 1,4-环己二烯 、 盐酸羟胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 3-{[((5R)-3-{4-[(acetyloxyamino)(imino)methyl]phenyl}-4,5-dihydro-5-isoxazolyl)acetyl]amino}-N-(4-benzyloxybutoxycarbonyl)-L-alanine
  参考文献：
  名称：

  Synthesis of N-Butyl Side Chain Hydroxylated Metabolites of Roxifiban, a Platelet Glycoprotein IIb/IIIa Receptor Antagonist

  摘要：

  Syntheses of three n-butyl side chain hydroxylated metabolites of Roxifiban (5, 6a and 6b) are reported. Initial use of benzyl as hydroxyl protecting group gave poor yield during its removal by catalytic hydrogenation, due to complication from N-O cleavage of the isoxazoline. This problem was eliminated by the use of TBDMS as the hydroxyl protecting group. The chemical structures of these metabolites as well as the intermediates have been fully characterized.

  DOI：

  10.3987/com-04-10087