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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (12): 2155-2158. 上一篇    下一篇

研究简报

(R)-2-{[4-(3-甲氧基丙氧基)-3-甲基吡啶-2-基]甲基亚硫酰基}- 1H-苯并咪唑的合成

徐宝财*; 刘家胜; 周雅文; 辛秀兰; 胡燕霞 ; 肖 阳   

  1. (北京工商大学化学与环境工程学院 北京 100037)
  • 收稿日期:2008-04-28 修回日期:2008-06-29 发布日期:2008-12-28
  • 通讯作者: 徐宝财

Synthesis of (R)-2-{[4-(3-Methoxypropoxy)-3-methyl-pyridin-2-yl]- methylsulfinyl}-1H-benzimidazole

XU, Bao-Cai*; LIU, Jia-Sheng ; ZHOU, Ya-Wen; XIN, Xiu-Lan;
HU, Yan-Xia; XIAO, Yang
  

  1. (School of Chemical and Environmental Engineering, Beijing Technology & Business University, Beijing 100037)
  • Received:2008-04-28 Revised:2008-06-29 Published:2008-12-28
  • Contact: XU, Bao-Cai

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以2,3-二甲基吡啶为起始原料, 经过11步反应, 不对称合成了质子泵抑制剂的关键中间体: (R)-2-{[4-(3-甲氧基丙氧基)-3-甲基吡啶-2-基]甲基亚硫酰基}-1H-苯并咪唑. 研究了用手性高效液相色谱拆分对映体、测定产品光学纯度的方法, 结果表明目标产品的ee值达到99%. 通过IR, UV, MS以及1H NMR分析对重要中间体和目标产品进行了结构鉴定.

关键词: 中间体, 2,3-二甲基吡啶, 合成, 质子泵抑制剂

A process for synthesis of (R)-2-{[4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl]methyl- sulfinyl}-1H-benzimidazole from 2,3-lutidine was studied. The optical purity of the product was analyzed by chiral high performance liquid chromatography (HPLC) and the enantiomeric excess value reached 99%. The structures of reaction intermediates and target product were characterized by IR, UV, MS and 1H NMR spectra.

Key words: intermediate, 2,3-lutidine, synthesis, proton pump inhibitor