Sodium Bicarbonate → HCID 69557930, compound

Participants

Reaction Steps

A solution of 2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzoimidazole-1-sulfonyl}phenoxy)butyric acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 11, 400 mg, 0.50 mmol) and NaHCO3 (47 mg, 0.55 mmol, 1.1 eq) in CH3CN-H2O (7 mL-3 mL) was heated to 70° C. for 3 h. Then volatile materials were removed by evaporation and the residual gummy oil was dissolved in CH3CN. The CH3CN solution was filtered to remove un-dissolved solids. The filtrate was dried and the residual yellow foam was treated with ether-EtOAc (5:1) to precipitate a solid. The solid was again treated with CH3CN, and the CH3CN solution was filtered to give 180 mg (58%) of 2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}phenoxy)butyric acid sodium salt (Compound 4 sodium salt). The sodium salt was dissolved in water, and acidified to pH 3 by 1 N HCl solution, and extracted with dichloromethane. The dichloromethane layer was evaporated to give Compound 4 as a free acid, which was further purified on a short silica gel column to yield 125 mg of 2-(4-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]benzimidazole-1-sulfonyl}phenoxy)butyric acid (Compound 4).

Provenance & Evidence