(S)-(-)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-(methanesulfonyloxy)propyl]-1,3-thiazolidin-4-one | 325172-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(-)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-(methanesulfonyloxy)propyl]-1,3-thiazolidin-4-one
• 英文别名: 3-[(2S)-2-(3,5-ditert-butyl-4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]propyl methanesulfonate
• CAS: 325172-11-0
• 化学式: C₂₁H₃₃NO₅S₂
• 分子量: 443.629
• InChiKey: SFGXSSMTXGOIBR-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-(-)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-(methanesulfonyloxy)propyl]-1,3-thiazolidin-4-one 在 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 17.25h， 生成 (-)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-[3,4-(methylenedioxy)phenoxy]ethyl]amino]propyl]-1,3-thiazolidin-4-one hydrogen fumarate salt
  参考文献：
  名称：

  Practical Synthesis of Novel Cardioprotective Drug, CP-060S

  摘要：

  A practical synthesis of a novel cardioprotective drug, CP-060S, is described. Key intermediate (S)-7, a chiral carboxylic acid, was prepared from 3,5-di-tert-butyl-4-hydroxybenzaldehyde 2 by employing thiazolidinone cyclocondensation followed by selective crystallization from a diastereomeric salt mixture which was prepared by treating racemic 7 with (S)-(-)-N-benzyl-alpha -methylbenzylamine 11. Racemization of the (R)-7-rich mixture, obtained from the mother liquid, by treatment with NaOH solution and subsequent resolution gave a second crop of (S) 7. Resolving agent 11 was efficiently recovered from the resolution process and pure enough for recycling use. Chiral acid (S)-7 was converted to the corresponding methyl ester (S)-1.4, which was reduced with NaBH4-CaCl2 to give alcohol intermediate (S)-4. Subsequent mesylation, amination, and salt formation with fumaric acid afforded CP-060S as pure enantiomer (99.8% ee) without any column chromatography.

  DOI：

  10.1021/op000096h
• 作为产物：
  描述：

  3-[(2S)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]propanoic acid 在 sodium tetrahydroborate 、 锂硼氢 、 三乙胺 、 calcium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 (S)-(-)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-(methanesulfonyloxy)propyl]-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Practical Synthesis of Novel Cardioprotective Drug, CP-060S

  摘要：

  A practical synthesis of a novel cardioprotective drug, CP-060S, is described. Key intermediate (S)-7, a chiral carboxylic acid, was prepared from 3,5-di-tert-butyl-4-hydroxybenzaldehyde 2 by employing thiazolidinone cyclocondensation followed by selective crystallization from a diastereomeric salt mixture which was prepared by treating racemic 7 with (S)-(-)-N-benzyl-alpha -methylbenzylamine 11. Racemization of the (R)-7-rich mixture, obtained from the mother liquid, by treatment with NaOH solution and subsequent resolution gave a second crop of (S) 7. Resolving agent 11 was efficiently recovered from the resolution process and pure enough for recycling use. Chiral acid (S)-7 was converted to the corresponding methyl ester (S)-1.4, which was reduced with NaBH4-CaCl2 to give alcohol intermediate (S)-4. Subsequent mesylation, amination, and salt formation with fumaric acid afforded CP-060S as pure enantiomer (99.8% ee) without any column chromatography.

  DOI：

  10.1021/op000096h

文献信息

• Practical Synthesis of Novel Cardioprotective Drug, CP-060<i>S</i>
  作者：Tatsuya Kato、Tomokazu Ozaki、Kouichi Tsuzuki、Nobuhiro Ohi

  DOI：10.1021/op000096h

  日期：2001.3.1

  A practical synthesis of a novel cardioprotective drug, CP-060S, is described. Key intermediate (S)-7, a chiral carboxylic acid, was prepared from 3,5-di-tert-butyl-4-hydroxybenzaldehyde 2 by employing thiazolidinone cyclocondensation followed by selective crystallization from a diastereomeric salt mixture which was prepared by treating racemic 7 with (S)-(-)-N-benzyl-alpha -methylbenzylamine 11. Racemization of the (R)-7-rich mixture, obtained from the mother liquid, by treatment with NaOH solution and subsequent resolution gave a second crop of (S) 7. Resolving agent 11 was efficiently recovered from the resolution process and pure enough for recycling use. Chiral acid (S)-7 was converted to the corresponding methyl ester (S)-1.4, which was reduced with NaBH4-CaCl2 to give alcohol intermediate (S)-4. Subsequent mesylation, amination, and salt formation with fumaric acid afforded CP-060S as pure enantiomer (99.8% ee) without any column chromatography.