Benzocaine → HCID 22056518, compound

Participants

Reaction Steps

Ethyl 4-aminobenzoate (910 mg, 5.50 mmol) and phenyl succinic anhydride (1070 mg, 6.00 mmol) were dissolved in 40 mL abs. CH3CN and stirred overnight at r.t. The solid precipitate was isolated and digirated with 2-propanol, dried in vacuum, dissolved in DCM and washed with citric acid. 4-{[4-(methoxycarbonyl)-phenyl]amino}-4-oxo-3-phenylbutanoic acid was isolated as a crystalline solid (980 mg, 2.88 mmol). M.p. 212° C.; TLC (cyclohexane/EtOAc 7/3) Rf 0.17; 1H NMR (400 MHz, D6-DMSO) δ 1.39 (t, J=7.2 Hz, 3H); 2.75 (dd, J=3.7 Hz, J=17.2 Hz, 1H); 3.42 (dd, J=3.7 Hz, J=17.2 Hz, 1H); 4.09 (dd, J=3.7 Hz, J=17.2 Hz, 1H); 4.35 (q, J=7.2 Hz, 2H); 7.33–7.41 (m, 5H), 7.75 (mc, 2H), 7.94 (mc, 2H). The regiochemistry was determined using NOESY NMR spectroscopy.

Provenance & Evidence