(R)-(-)-布洛芬(S)-(+)-赖氨酸酯 | 157369-85-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (R)-(-)-布洛芬(S)-(+)-赖氨酸酯
• 中文别名: 布洛芬杂质41
• 英文名称: ibuprofen L-lysine salt
• 英文别名: (R)-(-)-ibuprofen (S)-lysinate；(S)-ibuprofen-(R)-lysine；Ibuprofen lysine, (-)-；(2S)-2,6-diaminohexanoic acid;(2R)-2-[4-(2-methylpropyl)phenyl]propanoic acid
• CAS: 157369-85-2
• 化学式: C₆H₁₄N₂O₂*C₁₃H₁₈O₂
• 分子量: 352.474
• InChiKey: IHHXIUAEPKVVII-APFIOPMWSA-N

物化性质

• 熔点：
  185-187°C
• 溶解度：
  溶于甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-(-)-布洛芬(S)-(+)-赖氨酸酯 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以100%的产率得到(R)-(-)-布洛芬
  参考文献：
  名称：

  Temperature Selective Diastereo-Recognition (TSD):  Enantiomeric Ibuprofen via Environmentally Benign Selective Crystallization

  摘要：

  Selective crystallization of ibuprofen/lysinate from 1 mol of (R,S)-(racemic) ibuprofen and less than or equal to0.5 mol of (S)-lysine in aqueous ethanol affords either (S)-(+)-ibuprofen/(S)-lysinate or (R)-ibuprofen/(S)-lysinate (in preponderance) depending on the crystallization conditions. The previously unreported temperature selective diastereo-recognition (TSD) provides simple and efficient means to prepare either enantiomer of ibuprofen from (R,S)-ibuprofen utilizing the same commercially available inexpensive resolving agent, (S)-lysine. The unwanted enantiomeric ibuprofen could be recovered from the mother liquor and racemized by a simple, relatively waste-free thermal process. This racemization method when utilized in conjunction with the selective crystallization technology provides a simple, efficient, and eco-friendly means to prepare (S)-(+)-ibuprofen lysinate in an overall essentially quantitative yield. This technology also incorporates the fundamental principle of atom economy (via direct production of the preferred pharmaceutical salt of (S)-lysine).

  DOI：

  10.1021/op030203i
• 作为产物：
  描述：

  (2S)-2-(4-异丁基苯基)丙酸-L-赖氨酸水合物(1:1:1) 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 54.0h， 生成 (R)-(-)-布洛芬(S)-(+)-赖氨酸酯
  参考文献：
  名称：

  Temperature Selective Diastereo-Recognition (TSD):  Enantiomeric Ibuprofen via Environmentally Benign Selective Crystallization

  摘要：

  Selective crystallization of ibuprofen/lysinate from 1 mol of (R,S)-(racemic) ibuprofen and less than or equal to0.5 mol of (S)-lysine in aqueous ethanol affords either (S)-(+)-ibuprofen/(S)-lysinate or (R)-ibuprofen/(S)-lysinate (in preponderance) depending on the crystallization conditions. The previously unreported temperature selective diastereo-recognition (TSD) provides simple and efficient means to prepare either enantiomer of ibuprofen from (R,S)-ibuprofen utilizing the same commercially available inexpensive resolving agent, (S)-lysine. The unwanted enantiomeric ibuprofen could be recovered from the mother liquor and racemized by a simple, relatively waste-free thermal process. This racemization method when utilized in conjunction with the selective crystallization technology provides a simple, efficient, and eco-friendly means to prepare (S)-(+)-ibuprofen lysinate in an overall essentially quantitative yield. This technology also incorporates the fundamental principle of atom economy (via direct production of the preferred pharmaceutical salt of (S)-lysine).

  DOI：

  10.1021/op030203i

文献信息

• Acylmethanesulfonamides as new acylating agents for primary amines
  作者：Silvia Coniglio、Andrea Aramini、M.Candida Cesta、Sandro Colagioia、Roberto Curti、Fabrizio D'Alessandro、Gaetano D'Anniballe、Valerio D'Elia、Giuseppe Nano、Valerie Orlando、Marcello Allegretti

  DOI：10.1016/j.tetlet.2004.05.073

  日期：2004.7

  A new, simple and efficient procedure for the preparation of secondary amides through internal condensation of acylmethanesulfonamides ammonium salts is described. The selective acylation of mixed primary–secondary amines could be an attractive application of the new method.

  描述了一种通过酰基甲烷磺酰胺酰胺盐的内部缩合制备仲酰胺的新的，简单而有效的方法。混合的伯-仲胺的选择性酰化可能是新方法的诱人应用。
• IBUPROFEN-CAFFEINE COMBINATIONS
  申请人：MERCK & CO. INC.

  公开号：EP0663819A1

  公开（公告）日：1995-07-26
• EP0663839A4
  申请人：——

  公开号：EP0663839A4

  公开（公告）日：1998-06-03
• EP0663819A4
  申请人：——

  公开号：EP0663819A4

  公开（公告）日：1998-05-27
• IBUPROFEN-H 2? ANTAGONIST COMBINATIONS
  申请人：MERCK & CO. INC.

  公开号：EP0663839A1

  公开（公告）日：1995-07-26