Triethylamine → HCID 69833704, compound

Participants

Reaction Steps

A stirred solution of [3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetic acid (1.35 g, prepared as described in Example 52B of International Patent Application Publication No. WO 96/22966) in anhydrous tetrahydrofuran (60 ml), at 20° C. and under an atmosphere of argon, was treated with benzotriazol-lyloxytris(dimethylamino)phosphonium hexafluorophosphate (2.04 g). After stirring for 10 minutes the mixture was treated with 2-(4-amino-phenyl)-1-benzoyl-pyrrolidine-3-carboxylic acid methyl ester (1.5 g, Reference Example 14) then with triethylamine (1.77 ml) and dimethylaminopyridine (0.051 g). The resulting mixture was stirred at 20° C. for 60 hours then evaporated (40° C. and 2.7 kPa). The residue was dissolved in ethyl acetate (150 ml) and the solution was washed with water (100 ml), then with aqueous potassium bicarbonate solution (100 ml, 10%), then with water (50 ml), then dried over magnesium sulphate and then evaporated under reduced pressure (40° C., 2.7 kPa). The residue was subjected to flash chromatography on silica (200 g, 0.045-0.020 mm particle size) eluting with a mixture of cyclohexane and ethyl acetate (30:70, v/v) affording the title compound (0.33 g) as an off-white powder. MS [DCI (reactant gas, ammonia)]: 621 [M+H]+.

Provenance & Evidence