Sodium Bicarbonate → HCID 20786379, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-dimethyl-4-{2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}phenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 58, 1.6 g, 1.90 mmol) in 10 mL of CH3CN was added a solution of NaHCO3 (208 mg, 2.47 mmol, 1.3 eq) in 5 mL of H2O. The mixture was heated to 65° C. for 3 h. Thereafter all the volatile materials were removed under vacuum, the mixture was washed with EtOAc (2×), and then the aqueous layer was lyophilized overnight. The solid was dissolved in 80 mL of CH2Cl2, and then the mixture was filtered to remove insoluble material. The filtrate was concentrated and the residual oil was dissolved in 5 mL of CH2Cl2. EtOAc was added to the mixture to precipitate a white solid. The precipitate was collected by filtration, washed with EtOAc, and dried under vacuum to yield 800 mg (62%) of 3,5-dimethyl-4-{2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}phenoxyacetic acid sodium salt (Compound 33) as a white solid.

Provenance & Evidence