Aniline → HCID 57611859, compound

Participants

Reaction Steps

Crude potassium 2-[4-(tert-butoxycarbonyl)phenyl]-3-(dimethylamino)propanoate (925 mg, ˜2.79 mmol), EDCI (803 mg, 4.19 mmol), and HOBT (491 mg, 3.63 mg) were combined in DMF (15 mL) and stirred for 5 minutes before adding aniline (331 μL, 3.63 mmol). The reaction was stirred at room temperature for 3 h. Additional EDCI (200 mg) was added, and the reaction was stirred for another 3 h. The mixture was concentrated and purified by reverse phase HPLC (50-95% MeCN/water). The resulting residue was dissolved in EtOAc, neutralized with sat. NaHCO3, washed with brine, dried (MgSO4), and concentrated to give tert-butyl 4-{2-anilino-1-[(dimethylamino)methyl]-2-oxoethyl}benzoate as a white solid. 1H NMR (CDCl3) δ 7.97 (d, J=8.5 Hz, 2H), 7.33 (d, J=8.5 Hz, 2H), 7.21 (dd, J=8.5, 7.3 Hz, 2H), 6.77 (t, J=7.3 Hz, 1H), 6.72 (d, J=7.9 Hz, 2H), 4.22 (dd, J=8.8, 5.0 Hz, 1H), 3.80 (dd, J=13.8, 9.1 Hz, 1H), 3.40 (dd, J=13.6, 4.8 Hz, 1H), 2.95 (s, 3H), 2.74 (s, 3H), 1.58 (s, 9H). MS (ESI) calcd [M+H]+ 369.2, found 369.2.

Provenance & Evidence