Diethyl Ether → (R)-N-[4-(4-Acetamidophenylsulphonyl)-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

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Reaction Steps

Oxalyl chloride (0.047 ml) was added to a stirred suspension of (R)-(+)-2-hydroxy-2-methyl-3,3,3-trifluoropropanoic acid (Method 9) (0.077 g) in DCM (2.5 ml) containing DMF (1 drop). The mixture was stirred at ambient temperature for 2 hours and was then added to a solution of 4-(4-acetamidophenylsulphonyl)-2-chloroaniline (Method 10) (0.160 g) in DCM (2.5 ml) and stirred a further 2 hours. Ether (50 ml) was added and the mixture was washed with water (2×50 ml) and brine then dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-70% ethyl acetate/toluene to give the title compound (0.025 g) as a solid. NMR: 1.6 (s, 3H), 2.05 (s, 3H), 7.1-7.3 (brm, 1H), 7.8 (d, 2H), 7.9 (m, 3H), 7.97-8.05 (brs, 2H), 8.25 (d, 1H), 10.36 (brs, 1H); MS (ESP−): 463; EA: found: C, 47.8; H, 3.6; N, 5.4%; C18H16ClF3N2O5S.0.2 C7H8 requires: C, 48.2; H, 3.7; N, 5.8%.

Provenance & Evidence