Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

The TFA salt of the polar isomer of 1-[(3-chlorophenyl)(hydroxy)pyridin-3-ylacetyl]-N-[2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (0.01 g, 0.02 mmol) was partitioned between EtOAc and saturated sodium bicarbonate solution and extracted with EtOAc to retrieve the free base. To a stirred solution of the dried free base of 1-[(3-chlorophenyl)(hydroxy)pyridin-3-ylacetyl]-N-[2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (0.009 g, 0.017 mmol) in dichloromethane (1 mL), cooled to 0° C., was added 3-chloroperoxybenzoic acid 70% (0.006 g, 0.026 mmol). After 2 hours, the reaction was evaporated in vacuo and purified on a Gilson Preparative HPLC. Pure fractions were combined, freeze dried and lyophilized to yield the solid TFA salt of 1-[(3-chlorophenyl)(hydroxy)(1-oxidopyridin-3-yl)acetyl]-N-[2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (0.003 g, HPLC RT=2.70 min, Method A; LCMS m/z=534).

Provenance & Evidence