(2S)-2-(4-异丁基苯基)丙酸-L-赖氨酸水合物(1:1:1) | 113403-10-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (2S)-2-(4-异丁基苯基)丙酸-L-赖氨酸水合物(1:1:1)
• 英文名称: (S)-(+)-ibuprofen (S)-lysinate
• 英文别名: (S)-ibuprofen-(S)-lysine；S(+)-Ibuprofen lysinate；S(+)-ibuprofen-L-lysine；S-ibuprofen-S-lysinate；dexibuprofen lysinate；Dexibuprofen lysine anhydrous；(2S)-2,6-diaminohexanoic acid;(2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid
• CAS: 113403-10-4
• 化学式: C₆H₁₄N₂O₂*C₁₃H₁₈O₂
• 分子量: 352.474
• InChiKey: IHHXIUAEPKVVII-PTKYJSHISA-N

物化性质

• 溶解度：
  溶于甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 水 为溶剂， 反应 5.0h， 生成 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：

  (S)-(+)-布洛芬 以 乙醇 、 水 为溶剂， 反应 53.0h， 生成 (2S)-2-(4-异丁基苯基)丙酸-L-赖氨酸水合物(1:1:1)
  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
• 作为试剂：
  描述：

  布洛芬 、 L-赖氨酸 、 水 在 (2S)-2-(4-异丁基苯基)丙酸-L-赖氨酸水合物(1:1:1) 、 布洛芬 、 L-赖氨酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以This procedure resulted in the formation of 144 grams of 98.1-98.8% pure (S)-ibuprofen-(S)-lysine的产率得到(2S)-2-(4-异丁基苯基)丙酸-L-赖氨酸水合物(1:1:1)
  参考文献：
  名称：

  Formation and resolution of ibuprofen lysinate

  摘要：

  本发明揭示了一种制备和分离(S)-布洛芬-(S)-赖氨酸的方法。该方法采用优先结晶技术分离一对对映异构体盐，即(S)-布洛芬-(S)-赖氨酸盐和(R)-布洛芬-(S)-赖氨酸盐。

  公开号：

  US04994604A1

文献信息

• S(+)-ibuprofen-L-amino acid and S(+)-ibuprofen-D-amino acid as
  申请人：Merck & Co., Inc.

  公开号：US05200558A1

  公开（公告）日：1993-04-06

  S(+)-ibuprofen-L-amino acids and S(+)-ibuprofen-D-amino acids, substantially free of other ibuprofen-amino acid stereoisomers, give an onset-hastened, enhanced analgesic response in humans.

  S(+)-ibuprofen-L-氨基酸和S(+)-ibuprofen-D-氨基酸，基本上没有其他ibuprofen-氨基酸立体异构体，可以在人体中加速起效，增强镇痛作用。
• Sustained release with high and low viscosity HPMC
  申请人：Merck & Co., Inc.

  公开号：EP0440462B1

  公开（公告）日：1994-12-28
• IBUPROFEN-ANTITUSSIVE COMBINATIONS
  申请人：MERCK & CO. INC.

  公开号：EP0577772A1

  公开（公告）日：1994-01-12
• IBUPROFEN-CAFFEINE COMBINATIONS
  申请人：MERCK & CO. INC.

  公开号：EP0663819A1

  公开（公告）日：1995-07-26
• EP0663819A4
  申请人：——

  公开号：EP0663819A4

  公开（公告）日：1998-05-27