(S)-5-methoxy-2-[[(3,5-dimethyl-4-nitro-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (S)-5-methoxy-2-[[(3,5-dimethyl-4-nitro-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
• 英文别名: (S)-2-[[(4-nitro-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]5-methoxy-1H-benzimidazole；5-methoxy-2-[(S)-[(4-nitro-3,5-dimethylpyhdin-2-yl)methyl]sulfinyl]-1H-benzimidazole；(S)-2-(((3,5-Dimethyl-4-nitropyridin-2-yl)methyl)sulfinyl)-5-methoxy-1H-benzo[d]imidazole；2-[(S)-(3,5-dimethyl-4-nitropyridin-2-yl)methylsulfinyl]-6-methoxy-1H-benzimidazole
• 化学式: C₁₆H₁₆N₄O₄S
• 分子量: 360.393
• InChiKey: PFDONLPWKWJOCD-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-5-methoxy-2-[[(3,5-dimethyl-4-nitro-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole 在 甲醇 、 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 0.5h， 生成 5-methoxy-2-[(S)-[(4-nitro-3,5-dimethylpyhdin-2-yl)methyl]sulfinyl]-1H-benzimidazole sodium
  参考文献：
  名称：

  [EN] PREPARATION OF ESOMEPRAZOLE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS
  [FR] PRÉPARATION D'ÉSOMÉPRAZOLE ET DE SES SELS PHARMACEUTIQUEMENT ACCEPTABLES

  摘要：

  公开号：

  WO2010148314A3
• 作为产物：
  描述：

  5-甲氧基-2-(((3,5-二甲基-4-硝基-2-吡啶)甲基)硫代)-1H-苯并咪唑 以48%的产率得到
  参考文献：
  名称：

  New compounds useful for the synthesis of S- and R-omeprazole and a process for their preparation

  摘要：

  本发明涉及一种改进的奥美拉唑（omeprazole）（S）或（R）对映体合成方法，其特征在于将2-[[(4-X-3,5-二甲基吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑或2-[[(4-X-3,5-二甲基-1-氧代吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑（其中X是离去基团）氧化成相应的磺醇，该磺醇以结晶化合物的形式得到。对所得磺醇进行重结晶可得到化学和光学纯度更高的化合物，随后将其转化为（S）或（R）对映体的奥美拉唑。

  公开号：

  US20050187256A1

文献信息

• [EN] A PROCESS FOR THE PREPARATION OF SUBSTITITED PYRIDINYLMETHYLSULFINYL- BENZIMIDAZOLE ENANTIOMERS<br/>[FR] PROCEDE DE PREPARATION D'ENANTIOMERES DE PYRIDINYLMETHYLSULFINYL- BENZAMIDE SUBSTITUES
  申请人：HETERO DRUGS LTD

  公开号：WO2005054228A1

  公开（公告）日：2005-06-16

  The present invention provides an enantioselective process for preparing substituted benzimidazoles either as a single enantiomer or in an enantiomerically enriched form.

  本发明提供了一种手性选择性工艺，用于制备取代苯并咪唑，可以制备单一对映异构体或对映异构体富集的形式。
• New compounds useful for the synthesis of S- and R-omeprazole and a process for their preparation
  申请人：Unge Von Sverker

  公开号：US20050187256A1

  公开（公告）日：2005-08-25

  The present invention relates to an improved method for the synthesis of the (S)— or (R)-enantiomer of omeprazole, characterized in that 2-[[(4-X-3,5-dimethylpyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole or 2-[[(4-X-3,5-dimethyl-1-oxidopyridin-2-yl)methyl]thio]-5-methoxy- 1 H-benzimidazole, wherein X is a leaving group, is oxidized into the corresponding sulphoxide which is obtained as a crystalline compound. Recrystallisation of the thus obtained sulphoxide results in a compound of enhanced chemical and optical purity, which is subsequently transformed into the (S)- or (R)-enantiomer of omeprazole.

  本发明涉及一种改进的奥美拉唑(S或R)-对映体合成方法，其特征在于将2-[[(4-X-3,5-二甲基吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑或2-[[(4-X-3,5-二甲基-1-氧代吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑（其中X是离去基团）氧化成相应的亚砜，并以晶体化合物的形式得到。对所得亚砜进行重结晶可得到化学和光学纯度更高的化合物，随后将其转化为奥美拉唑的(S)或(R)-对映体。
• New Compounds Useful for the Synthesis of S- and R-Omeprazole and a Process for Their Preparation
  申请人：von Unge Sverker

  公开号：US20090253911A1

  公开（公告）日：2009-10-08

  The present invention relates to an improved method for the synthesis of the (S)- or (R)-enantiomer of omeprazole, characterized in that 2-[[(4-X-3,5-dimethylpyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole or 2-[[(4-X-3,5-dimethyl-1-oxidopyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole, wherein X is a leaving group, is oxidized into the corresponding sulphoxide which is obtained as a crystalline compound. Recrystallisation of the thus obtained sulphoxide results in a compound of enhanced chemical and optical purity, which is subsequently transformed into the (S)- or (R)-enantiomer of omeprazole.

  本发明涉及一种改进的奥美拉唑（omeprazole）（S）或（R）对映体合成方法，其特征在于将2-[[(4-X-3,5-二甲基吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑或2-[[(4-X-3,5-二甲基-1-氧代吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑，其中X是一个离去基团，氧化为相应的磺酸氧化物，该磺酸氧化物以晶体化合物的形式获得。因此获得的磺酸氧化物再结晶，可得到化学和光学纯度更高的化合物，随后转化为奥美拉唑（S）或（R）对映体。
• Compounds Useful for the Synthesis of S- and R-Omeprazole and a Process for Their Preparation
  申请人：Fregler Christina

  公开号：US20080255199A1

  公开（公告）日：2008-10-16

  The present invention relates to an improved method for the synthesis of the (S)- or (R)-enantiomer of omeprazole, characterized in that 2-[[(4-X-3,5-dimethylpyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole or 2-[[(4-X-3,5-dimethyl-1-ox-idopyridin-2-yl) methyl]thio]-5-methoxy-1H-benzimidazole, wherein X is a leaving group, is oxidized into the corresponding sulphoxide which is obtained as a crystalline compound. Recrystallisation of the thus obtained sulphoxide results in a compound of enhanced chemical and optical purity, which is subsequently transformed into the (S)- or (R)-enantiomer of omeprazole.

  本发明涉及一种改进的奥美拉唑（omeprazole）（S）或（R）对映体合成方法，其特征在于将2-[[(4-X-3,5-二甲基吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑或2-[[(4-X-3,5-二甲基-1-氧代吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑（其中X是一个离去基团）氧化成相应的亚砜，该亚砜以结晶化合物的形式得到。因此获得的亚砜再结晶可得到化学和光学纯度提高的化合物，随后将其转化为（S）或（R）对映体的奥美拉唑。
• Compounds Useful for the Synthesis of S- and R-Omeprazole and a Process for their Preparation
  申请人：Unge Von Sverker

  公开号：US20070161682A1

  公开（公告）日：2007-07-12

  The present invention relates to an improved method for the synthesis of the (S)- or (R)-enantiomer of omeprazole, characterized in that 2-[[(4-X-3,5-dimethylpyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole or 2-[[(4-X-3,5-dimethyl-1-oxidopyridin-2-yl)methyl]thio]-5-methoxy-1H-benzimidazole, wherein X is a leaving group, is oxidized into the corresponding sulphoxide which is obtained as a crystalline compound. Recrystallisation of the thus obtained sulphoxide results in a compound of enhanced chemical and optical purity, which is subsequently transformed into the (S)- or (R)-enantiomer of omeprazole.

  本发明涉及一种改进的奥美拉唑（omeprazole）的(S)-或(R)-对映体合成方法，其特征在于将2-[[(4-X-3,5-二甲基吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑或2-[[(4-X-3,5-二甲基-1-氧代吡啶-2-基)甲基]硫基]-5-甲氧基-1H-苯并咪唑（其中X为离去基）氧化为相应的亚砜，所得的亚砜为结晶化合物。因此得到的亚砜经再结晶后，可得到化学和光学纯度更高的化合物，随后转化为(S)-或(R)-奥美拉唑的对映体。