1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 2-[4-({[2-[(tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)phenyl]-3-{[(methylamino)carbonyl]-amino}propanoate

Participants

Reaction Steps

4-[2-Methoxy-1-({[(methylamino)carbonyl]amino}-methyl)-2-oxoethyl]benzoic acid (350 mg, 1.25 mmol), EDCI (312 mg, 1.63 mmol), and HOBT (220 mg, 1.63 mmol) were combined in DMF (15 mL) and stirred for 10 minutes before adding tert-butyl [2-amino-4-(3-thienyl)phenyl]carbamate (398 mg, 1.37 mmol). The reaction was then stirred at 55° C. for 24 h. The solvent was evaporated, and the resulting residue was dissolved in EtOAc, washed (water, brine), dried (MgSO4), and concentrated. Flash chromatography on silica (0-5% MeOH/CH2Cl2) afforded methyl 2-[4-({[2-[(tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)phenyl]-3-{[(methylamino)carbonyl]amino}propanoate as a white solid. MS (ESI) calcd [M+H]+ 553.2, found 553.2.

Provenance & Evidence