Benzoyl isothiocyanate → N-(((3S,4R,5S)-3-(2,4-difluorophenyl)-4-(hydroxymethyl)-5-((trityloxy)methyl)tetrahydrofuran-3-yl)carbamothioyl)benzamide

Participants

Reaction Steps

Benzoyl isothiocyanate (1.24 mL, 9.2 mmol) was added to a stirred solution of ((2S,3R,4S)-4-amino-4-(2,4-difluorophenyl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl)methanol (4.2 g, 8.4 mmol) in dry DCM (20 mL) at RT under nitrogen. After 1 hour the volatiles were removed in vacuo and then the residue was purified by column chromatography (normal phase, 100 g, Biotage SNAP cartridge KP-Sil, 50 mL per min, gradient 5% to 30% EtOAc in n-hexane) to give the title compound (5.4 g). 1H NMR (400 MHz, MeOH-d4) δ ppm: 2.71-2.83 (m, 1 H) 3.12 (dd, J=10.15, 4.52 Hz, 1 H) 3.27 (dd, J=10.15, 3.67 Hz, 1 H) 3.83 (d, J=5.26 Hz, 2 H) 4.19-4.27 (m, 1 H) 4.55 (d, J=9.78 Hz, 1 H) 5.18 (d, J=9.78 Hz, 1 H) 6.82-6.96 (m, 2 H) 7.17-7.32 (m, 9 H) 7.36-7.41 (m, 6 H) 7.49-7.57 (m, 3 H) 7.60-7.67 (m, 1 H) 7.89-7.94 (m, 2 H),

Provenance & Evidence