Sodium Bicarbonate → 3-[2-Methoxy-5-{2-(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl)-benzimidazole-1-sulfonyl}phenyl]propionic acid sodium salt

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[2-methoxy-5-{2-(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl)-benzimidazole-1-sulfonyl}phenyl]propionic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 63, 1.0 g, 1.26 mmol) in 10 mL of CH3CN was added the solution of NaHCO3 (127 mg, 1.51 mmol, 1.2 eq) in 5 mL of H2O. The mixture was heated to 65° C. for 4 h. Thereafter all the volatile materials were removed under vacuum, the mixture was washed with Et2O-EtOAc (10:1)), and then the aqueous layer was lyophilized overnight. The solid was dissolved in 100 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. Et2O was added to the mixture to precipitate a white solid. The precipitate was filtered, washed with Et2O, and dried under vacuum to yield 730 mg (91%) of 3-[2-methoxy-5-{2-(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-methanesulfinyl)-benzimidazole-1-sulfonyl}phenyl]propionic acid sodium salt (Compound 36) as a white solid.

Provenance & Evidence