Trifluoroacetic acid → HCID 23512271, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-[N′-(2-benzyloxyphenyl)ureido]-3-methoxyphenylacetate (2.35 g, 5.08 mmol) in CH2Cl2 (25 mL) was added TFA (25 mL) at 0° C. After being stirred at room temperature for 3 hr, the mixture was concentrated. The residue was dissolved in 1 N NaOH and washed with Et2O. The basic water layer was poured into ice-1 N HCl and the resulting mixture was extracted with CHCl3-MeOH (4:1, v/v). The extracts were washed with brine, dried over Na2SO4, and concentrated to dryness. The residue was dissolved in isopropyl ether and hexane was added to this solution until the crystallization was completed. The solid was collected to give 4-[N′-(2-benzyloxyphenyl)ureido]-3-methoxyphenylacetic acid (1.59 g, 77%) as a brownish solid. 1H-NMR (DMSO-d6) δ 3.50 (s, 2H), 3.85 (s, 3H), 5.26 (s, 2H), 6.76 (d, J=8.3 Hz, 1H), 6.83–6.89 (m, 2H), 6.91 (s, 1H), 7.01 (dd, J=8.3, 2.3 Hz, 1H), 7.31 (t, J=7.3 Hz, 1H), 7.39 (t, J=7.3 Hz, 2H), 7.49 (d, J=7.3 Hz, 2H), 7.97 (d, J=8.3 Hz, 1H), 8.04 (d, J=8.3 Hz, 1H), 8.80 (s, 1H), 8.86 (s, 1H), 12.24 (broad s, 1H); FAB-MS m/z 407 (M++1).

Provenance & Evidence