Potassium Carbonate → HCID 178521055, compound

Participants

Reaction Steps

(5R,6S,7R)-5-(acetoxymethyl)-2-(2,2-difluoroethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (0.209 g, 0.51 mmol) was dissolved in anhydrous MeOH. Solid K2CO3 was added to the solution until it was basic, and the reaction was stirred at room temperature (1.5 h). The reaction was filtered and then concentrated in vacuo. The resulting oil was purified via flash column chromatography with a solvent system of 5:1 DCM and MeOH, providing (5R,6S,7R)-2-(2-fluoroethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (37) (0.106 g, 74% yield),1H NMR (500 MHz, methanol-d4) δ 3.26-3.27 (m, 1H), 3.43-3.46 (m, 1H), 3.51-3.56 (m, 2H), 3.58-3.61 (m, 1H), 3.74 (dd, 1H, J=2.3, 11.9 Hz), 3.93 (t, 1H, J=5.4 Hz), 4.08 (t, 1H, J=6.0 Hz), 6.01 (tt, 1H, J=4.3, 56.4 Hz), 6.34 (d, 1H, J=6.4 Hz). 13C NMR (125 MHz, methanol-d4) δ 58.84, 69.85, 74.23, 75.17, 90.09, 114.19 (t, JC-F=241 Hz), 161.92.

Provenance & Evidence