Water → 2-Methoxy-5-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]benzimidazole-1-sulfonyl}-benzoic acid sodium salt

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Reaction Conditions

Reaction Steps

A mixture of 2-methoxy-5-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}benzoic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 8, 400 mg, 0.52 mmol) and NaHCO3 (52 mg, 0.62 mmol, 1.2 eq) in CH3CN (3 mL)-H2O (2 mL)-i-PrOH (1 mL) was heated to 70° C. for 1.5 h. Then volatile materials were removed by evaporation and the residual oil was dissolved in CH2Cl2-MeOH, the mixture was filtered to remove insoluble solids. The filtrate was concentrated by evaporation. The residual syrup was dissolved in H2O, and the mixture was extracted with CH2Cl2 (2 times) to remove the starting material, lansoprazole and tolyl vinyl sulfone. The water solution was freeze-dried to yield 200 mg (65%) Compound 3 sodium salt as a light yellow solid.

Provenance & Evidence