Benzoyl chloride → HCID 66551752, compound

Participants

Reaction Steps

A solution of (3aR,5R,6S,7R,7aR)-2-amino-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (110 mg, 0.50 mmol) in THF (20 mL) and saturated aqueous NaHCO3 (5 mL) was treated with benzoyl chloride (77 mg, 0.55 mmol) for 1 hour at 0° C. After filtration, the solution was concentrated under vacuum to give a residue, which was purified by Prep-HPLC with the following conditions [(Agilent 1200 prep HPLC): Column, SunFire Prep C18,19*50 mm Sum; mobile phase, WATER with 0.03% NH4OH and CH3CN(10% CH3CN up to 45% in 10 min); Detector, UV 220 nm;] to give the title compound as a white solid (39.3 mg, 24%). (ES, m/z)[M+H]+324.9; 1H NMR (300 MHz, D2O) δ 7.83-7.85 (d, J=7.5 Hz, 2H), 7.49-7.54 (m, 1H), 7.36-7.42 (m, 2H), 6.13-6.15 (d, J=6.3 Hz, 1H), 3.97-4.02 (dd, J=6.3 Hz, 6.9 Hz, 1H), 3.89-3.93 (t, J=5.7 Hz, 1H), 3.45-3.73 (m, 4H).

Provenance & Evidence