Dimethylformamide → tert-Butyl 3-methoxybenzyl((2R,3S)-3-(3-acetyl-5-(benzamido)benzamido)-4-(3,5-difluorophenyl)-2-hydroxybutyl)carbamate

Participants

Reaction Steps

A mixture of 3-acetyl-5-(dipropylcarbamoyl)benzoic acid (95 mg, 0.326 mmol), HATU (149 mg, 0.392 mmol) and Hunig's base (168.8 mg, 0.2 mL, 1.306 mmol) in DMF (2.9 mL) was stirred for 10 min and then tert-butyl 3-methoxybenzyl((2R,3S)-3-amino-4-(3,5-difluorophenyl)-2-hydroxybutyl)-carbamate (142 mg, 0.326 mmol) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with H2O 3 times. The organic layer was dried over sodium sulfate and concentrated under vacuum to give the title compound (220 mg) which was ready for next step without further purification: 1H NMR (CD3OD, 500 MHz) δ ppm 0.71 (3H, m), 1.02 (3H, m), 1.48-1.55 (11H, m), 1.74-1.76 (2H, m), 2.66 (2H, m), 2.87 (1H, m), 3.11-3.17 (3H, m), 3.33 (1H, m), 3.50 (2H, m), 3.76 (4H, m), 3.98 (1H, m), 4.32 (1H, m), 4.42-4.45 (1H, m), 4.68-4.82 (2H, m), 6.70-6.74 (1H, m), 6.80 (3H, m), 6.90 (2H, m), 7.22 (1H, m), 7.51-7.87 (1H, m), 8.07 (1H, m), 8.36-8.56 (1H, m). HPLC retention time: 2.195 min (method B). MS (ESI) (M+H)+ 710.31.

Provenance & Evidence