1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Carbonate tert-butyl [2-({4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)phenyl]carbamate

Participants

Reaction Steps

To a solution of 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid (110 mg, 0.29 mmol) in DMF (2 mL) at room temperature was added EDCI (67 mg, 0.35 mmol) and HOBT (48 mg, 0.36 mmol). The solution was stirred for 30 min and tert-butyl (2-aminophenyl)carbamate (85 mg, 0.41 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 20 h and purified by reverse phase HPLC (30% to 95% MeCN in water) to give carbonate tert-butyl [2-({4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)phenyl]carbamate (105 mg, 64%) as a white solid: 1H NMR (600 MHz, DMSO-d6) δ 10.27 (s br, 2H), 9.83 (s br, 1H), 8.64 (s br, 1H), 7.94 (d, J=8.2 Hz, 2H), 7.60-7.58 (m, 6H), 7.53 (t, J=8.8 Hz, 2H), 7.31 (t, J=8.1 Hz, 41-1), 7.19 (td, J=7.6, 1.5 Hz, 1H), 7.13 (td, J=7.6, 1.5 Hz, 1H), 7.06 (t, J=7.3 Hz, 2H), 4.98 (s, 1H), 1.42 (s, 9H); ESIMS calcd 587.2 (M++Na), found 587.2 (M++Na).

Provenance & Evidence