Sodium Bicarbonate → HCID 69882460, compound

Participants

Reaction Conditions

Reaction Steps

Iron (324 mg) and conc. hydrochloric acid (1 drop) was added to a suspension of (R)-N-{2-chloro-3-nitro-4-[4-(N,N-dimethylcarbamoyl)phenyl]sulphonylphenyl}-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 63) (305 mg) in water (0.25 ml) and EtOH (1 ml). The mixture was stirred for 1.5 hours at 75° C. and allowed to cool to ambient temperature. Saturated NaHCO3 (10 ml) was added and the solution was extracted with EtOAc (100 ml). The extracts were washed with brine (40 ml) and dried. The volatile material was removed by evaporation. The reaction had not gone to completion, so additional iron (324 mg) and conc. hydrochloric acid (3 drop) was added to a suspension of the residue in water (0.25 ml) and EtOH (1 ml). The mixture was stirred for 3 hours at 75° C. After the mixture was allowed to cool to ambient temperature, saturated NaHCO3 (10 ml) was added and the solution was extracted with EtOAc (100 ml). The extracts were washed with brine (40 ml) and dried. The volatile material was removed by evaporation to give a foam. This was purified by chromatography on silica gel, eluted with 4% MeOH in DCM to give the title compound as a foam (250 mg). NMR: 1.58 (s, 3H), 2.81 (s, 3H), 2.95 (s, 3H), 6.31 (s, 2), 7.60 (m, 3H), 7.81 (d, 1H), 7.96 (m, 3H), 9.73 (brs, 1H), m/z 492.

Provenance & Evidence