Trifluoroacetic acid → 4-[2-Anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid

Participants

Reaction Steps

To a solution of tert-butyl 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoate, prepared in the previous step, in CH2Cl2 (200 mL) at room temperature was added trifluoroacetic acid (50 mL). The reaction mixture was stirred at room temperature for 2 h and concentrated. The crude acid was dissolved in CH2Cl2, filtered, and precipitated with hexanes. The solid was collected by filtration, washed with hexanes, and dried under high vacuum to yield 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid (7.58 g, 71% from dimethyl [4-(tert-butoxycarbonyl)phenyl]malonate) as an off white solid: 1H NMR (600 MHz, DMSO-d6) δ 12.94 (s br, 1H), 10.26 (s br, 2H), 7.94 (d, J=8.2 Hz, 2H), 7.58 (d, J=7.6 Hz, 4H), 7.54 (d, J=8.2 Hz, 2H), 7.30 (t, J=7.6 Hz, 41-1), 7.05 (t, J=7.3 Hz, 2H), 4.97 (s, 1H); ESIMS calcd 375.1 (M++H), found 375.1 (M++H).

Provenance & Evidence