Lansoprazole → 3-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}benzoic Acid 2-(3-nitro-benzenesulfonyl)ethyl Ester

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Reaction Steps

To a heterogeneous mixture of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]-1H-benzimidazole (600 mg, 1.62 mmol) in CH2Cl (10 mL) was added NaH (45 mg, 1.95 mmol) at room temperature, resulting in a clear solution. To this clear mixture was added the sulfonyl chloride (Intermediate 1, 845 mg, 1.95 mmol, 1.2 eq), in CH2Cl2 at room temperature, and then the mixture was stirred for 2 h. Thereafter water was added and the mixture was extracted with CH2Cl2, and the organic layers were dried and concentrated. The residual oil was purified by column chromatography (3% MeOH in CH2Cl2) to yield 1.0 g (80%) of yellow foam.

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