Trifluoroacetic acid → 4-[N'-(2-fluorophenyl)ureido]-3-methylphenylacetic acid

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-[N′-(2-fluorophenyl)ureido]-3-methylphenylacetate (1.25 g, 3.49 mmol) in CH2Cl2 (10 ml) was added TFA (10 ml) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated to a small volume and poured into ice-H2O. The resulting precipitate was collected under a reduced pressure and the crude solid was recrystallized from MeOH—CHCl3-IPE to give 4-[N′-(2-fluorophenyl)ureido]-3-methylphenylacetic acid (830 mg, 79%) as white needles. 1H-NMR (DMSO-d6) δ 2.23 (s, 3 H), 3.47 (s, 2 H), 6.96–7.30 (m, 5 H), 7.74–7.76 (m, 1 H), 8.17–8.20 (m, 1 H), 8.33 (s, 1 H), 8.94 (s, 1 H), 12.27 (br s, 1 H); Anal. Calcd for C16H15FN2O3: C, 63.57; H, 5.00; N, 9.27; F, 6.28. Found: C, 63.28; H, 5.00; N, 9.14; F, 6.43.

Provenance & Evidence