Benzoyl chloride → HCID 69083776, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (5 g, 20 mmol) in pyridine (150 mL) was added a solution of benzoyl chloride (3.4 g, 24 mmol) in dichloromethane (10 mL) at 0° C. within 10 minutes, and then stirred for 5 hours at 0° C. in an ice/salt bath. The reaction was quenched by the addition of saturated aqueous NaHCO3 solution (100 mL), and extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (2×20 mL), dried over sodium sulfate, filtered and concentrated under vacuum. The crude residue was purified by flash column chromatography with 2% 5% methanol in dichloromethane to afford the title compound as an off-white solid (4.5 g, 63%). (ES, m/z): [M+H]+ 353.0; 1H NMR (300 MHz, CD3OD) δ 8.07-8.01 (m, 2H), 7.99-7.40 (m, 3H), 6.43 (d, J=6.6 Hz, 1H), 4.88-4.85 (m, 1H), 4.63-4.45 (m, 1H), 4.19-4.15 (m, 1H), 3.99-3.93 (m, 2H), 3.36-3.32 (m, 1H), 3.06 (s, 6H).

Provenance & Evidence