1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl [2-[(4-{[(acetylamino)methyl]-2-anilino-2-oxoethyl}benzoyl)amino]-4-(3-thienyl)phenyl]carbamate

Participants

Reaction Steps

4-{1-[(Acetylamino)methyl]-2-anilino-2-oxoethyl}benzoic acid (232 mg, 0.71 mmol), EDCI (176 mg, 0.92 mmol), and HOBT (124 mg, 0.92 mmol) were combined in DMF (8 mL) and stirred for 10 minutes before adding tert-butyl [2-amino-4-(3-thienyl)phenyl]carbamate (227 mg, 0.78 mmol). The reaction was then stirred at 60° C. for 24 h. The solution was cooled to room temperature, poured into water (40 mL), and filtered to collect an orange solid. The crude solid was dissolved in CH2Cl2 (25 mL) and hexanes (20 mL), concentrated to half volume, and filtered to give tert-butyl[2-[(4-{1-[(acetylamino)methyl]-2-anilino-2-oxoethyl}benzoyl)amino]-4-(3-thienyl)phenyl]carbamate as a white solid. MS (ESI) calcd [M+H]+ 599.2, found 599.1.

Provenance & Evidence