Water → (2-(2-Benzenesulfonyl-ethoxycarbonylmethoxy)-4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)acetic Acid 2-benzenesulfonyl-ethyl Ester

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Reaction Steps

To a heterogeneous mixture of 2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)pyridin-2-ylmethanesulfinyl]-benzimidazole, (LANSOPRAZOLE) (500 mg, 1.35 mmol) in CH2Cl2 (10 mL) was added NaH (40 mg, 1.63 mmol) at room temperature resulting in a clear solution. To this clear mixture was added [2-(2-benzenesulfonyl-ethoxycarbonylmethoxy)-4-chlorosulfonyl-phenoxy]-acetic acid 2-benzenesulfonyl-ethyl ester (Intermediate 29, 1.0 g, 1.63 mmol, 1.2 eq) in CH2Cl2 (5 mL) at room temperature, and the mixture was stirred for 3 h. Thereafter water was added, the mixture was extracted with CH2Cl2, and the organic layers were dried and concentrated under reduced pressure. The residual oil was purified by column chromatography (CH2Cl2 to 2% MeOH in CH2Cl2) to yield Intermediate 30 (1.05 g, 78%) as an off-white foam.

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