Oxalyl chloride → (R)-N-(4-[Anilinosulphonyl]-2,5-dimethoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

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Reaction Steps

Oxalyl chloride (0.13 ml, 1.5 mmol) was added to a stirred suspension of (R)-(+)-2-hydroxy-2-methyl-3,3,3-trifluoropropanoic acid (0.154 g, 0.97 mmol) (Method 3) in DCM (10 ml) containing DMF (1 drop). The mixture was stirred at ambient temperature overnight, then 4-[anilinosulphonyl]-2,5-dimethoxyaniline (200 mg, 0.65 mmol)† and 2,6-di-t-butylpyridine (0.14 ml, 0.66 mmol) was added and the resulting mixture stirred a further 2 hours at room temperature. Dichloromethane (25 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 50% EtOAc/iso-hexane to give the title compound as a solid (0.125 g, 0.28 mmol); M.p: 194-195° C., NMR: 1.7 (s, 3H), 3.8 (s, 3H), 4.1 (s, 3H), 6.9 (s, 1H), 7.05 (m, 3H), 7.2 (m, 3H), 8.3 (s, 1H), 9.1 (brs, 1H); m/z 447.

Provenance & Evidence