5-methoxy-2-[(S)-[(4-chloro-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole | 863029-88-3

• 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: 5-methoxy-2-[(S)-[(4-chloro-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole
• 英文别名: (S)-2-[[(4-chloro-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]5-methoxy-1H-benzimidazole；2-[(S)-(4-chloro-3,5-dimethylpyridin-2-yl)methylsulfinyl]-6-methoxy-1H-benzimidazole
• CAS: 863029-88-3
• 化学式: C₁₆H₁₆ClN₃O₂S
• 分子量: 349.841
• InChiKey: LZEPUBIBIWJUSW-QHCPKHFHSA-N

物化性质

• 沸点：
  597.9±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 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：
  87.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯甲基-3,5-二甲基-4-甲氧基吡啶盐酸盐 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 22.5h， 生成 5-methoxy-2-[(S)-[(4-chloro-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole
  参考文献：
  名称：

  一种艾司奥美拉唑杂质制备的方法

  摘要：

  本发明公开了一种艾司奥美拉唑杂质制备的方法，以2‑氯甲基‑4‑甲氧基‑3,5‑二甲基吡啶盐酸盐为起始原料，经过脱甲基、卤代、缩合及不对称氧化得到5‑甲氧基‑2‑[(S)‑[(4‑氯‑3,5‑二甲基‑2‑吡啶基）甲基]亚硫酰基]‑1H‑苯并咪唑（II）。该合成路线简短，起始原料易得，反应条件温和，操作简便，不需要柱层析即可得到上述的杂质，所制备的杂质纯度可达到99%以上，ee值可达到99%以上，可作为对照品用于质量研究。

  公开号：

  CN108484578B

文献信息

• [EN] A PROCESS FOR THE PREPARATION OF AMORPHOUS ESOMEPRAZOLE<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ÉSOMÉPRAZOLE AMORPHE
  申请人：GLENMARK GENERICS LTD

  公开号：WO2011095984A1

  公开（公告）日：2011-08-11

  The present invention relates to a process for the preparation of esomeprazole in amorphous form by spray drying.

  本发明涉及一种通过喷雾干燥制备非晶态埃索美拉唑的方法。
• 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。