A New Synthetic Process of Lansoprazole
Abstract
Lansoprazole is the generic name of 2-[[[3-Methyl-4(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1 H-benzimidazole, 1 (see Scheme 1). It is a proton pump inhibitor that reduces gastric acid secretion and has successfully been used to heal and relieve symptoms of gastric or duodenal ulcers and gastro-esophagal reflux. 1 Lansoprazole has been synthesized by an oxidation of sulfide 9 produced from a substitution reaction between 2mercaptobenzimidazole and pyridine derivatives such as 2chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine, 8. 2,3 The transformation of sulfide 9 into lansoprazole has been generally carried out with peroxyacid such as mCPBA or hydrogen peroxide in the presence of homogeneous catalyst. 3 Recently, we found that trirutile type solid oxides catalyze the hydrogen peroxide oxidation of sulfides to sulfoxides very efficiently. 4 The reaction was very selective producing sulfoxide with negligible amount of sulfone. Since the reaction is performed under heterogeneous conditions, the solid catalyst can be easily recovered by a simple filtration of the final reaction mixture. Because of these advantages in purification of the product, we decided to apply the heterogeneous sulfoxidation method to the synthesis of lansoprazole. In our approach to the synthesis of lansoprazole, we tried to devise a new process that could use 3-picoline as a starting material because it is more readily available than 2,3-lutidine, the most widely used starting material.…
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