Hydrochloric Acid → [2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclopropyl-acetic acid

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Reaction Steps

To a ice-cold suspension of 10.15 g (21.11 mmol) N-benzyl-N-nitroso-2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclopropyl-acetamide in 60 ml tetrahydrofuran and 15 ml water were added dropwise over 30 min. a solution of 8.86 g (211 mmol) lithium hydroxide monohydrate in 43.1 ml (422 mmol) hydrogen peroxide 30% solution and 30 ml water. After stirring for 2.25 h at room temperature the pH was adjusted to 3 using 70 ml acetic acid and 25% aqueous hydrochloric acid. The resulting light yellow solution was extracted three times with ethyl acetate. The organic layers were washed with water, aqueous saturated sodium bicarbonate solution and brine. After drying over magnesium sulfate and filtration, the solution was evaporated until a suspension formed. This suspension was filtered and washed with ethyl acetate to give the compound as a white solid (56%). MS (Turbo Spray): m/z=363.2 [M+H].

Provenance & Evidence