Triethylamine → HCID 54191973, compound

Participants

Reaction Steps

A solution of 10.6 g (34.3 mmol) of 4-methylamino-5,5-diphenyl-pent-2-enoic acid ethyl ester in 110 ml of methylene chloride is added at 0° C. via a cannula to a solution of 6.7 ml (36.0 mmol) of 3,5-bistrifluoromethyl-benzoyl chloride in 110 ml of methylene chloride. 5.8 ml (41.1 mmol) of triethylamine and 0.4 g (3.4 mmol) of 4-dimethylaminopyridine are then added. After 1 hour the reaction mixture is diluted with ethyl acetate and washed twice with water and once with brine. The aqueous phases are back-extracted once with ethyl acetate. The combined organic phases are then dried over magnesium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with methylene chloride/methanol (100:0 to 98:2). The title compound is obtained in the form of a light-yellow foam. TLC: methylene chloride/methanol (98:2) Rf =0.38; Rt (HPLC)=22.4 min; 1H-NMR (400 MHz, d6 -DMSO, 120° C.) d 8.00 (br, 1H), 7.47-7.29 (m, 10H), 7.26-7.20 (m, 2H), 6.83 (dd, 1H), 5.96 (d, 1H), 5.89 (br, 1H), 4.65 (d, 1H), 4.10 (q, 2H), 2.68 (s, 3H), 1.18 (t, 3H); FAB-MS (M+H)+ =550.

Provenance & Evidence