Sodium borohydride → tert-butyl 3-methoxybenzyl((2R,3S)-3-(3-(benzamido)-5-(1-hydroxyethyl)benzamido)-4-(3,5-difluorophenyl)-2-hydroxybutyl)carbamate

Participants

Reaction Steps

tert-Butyl 3-methoxybenzyl((2R,3S)-3-(3-acetyl-5-(benzamido)benzamido)-4-(3,5-difluorophenyl)-2-hydroxybutyl)carbamate (20 mg, 0.0282 mmol) was dissolved in MeOH (0.2 mL) and sodium borohydride (1.43 mg, 0.0378 mmol) was added. The reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated and partitioned between ethyl acetate and H2O. The organic layer was separated and purified by reverse phase prep HPLC to give the title compound (15 mg): 1H NMR (CD3OD, 500 MHz) δ ppm 0.71 (3H, t, J=5 Hz), 1.02 (3H, m), 1.45-1.47 (2H, m), 1.54 (2H, m), 1.74 (2H, m), 2.85 (1H, m), 3.09-3.18 (3H, m), 3.28 (1H, m), 3.49 (2H, m), 3.72-3.81 (4H, m), 3.97 (1H, m), 4.29 (1H, m), 4.41-4.44 (1H, m), 4.75 (1H, m), 4.90 (1H, m), 6.71 (1H, m), 6.81-6.82 (3H, m), 6.89 (2H, m), 7.22 (1H, m), 7.49-7.52 (2H, m), 7.76 (1H, m). HPLC retention time: 2.223 min (method A). MS (ESI) (M+H)+ 712.57.

Provenance & Evidence