Hydrochloric Acid → HCID 57520941, compound

Participants

Reaction Steps

To a solution of tert-butyl (-(3aR,5R,6R,7S,7aR)-5-(((tert-butyldimethylsilyl)oxy)methyl)-7-fluoro-6-hydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)(methyl)carbamate (0.200 g, 0.444 mmol) in dry MeOH (6 mL) was bubbled HCl gas for 30 sec. The mixture was stirred at room temperature for 5 h. After the solvent was evaporated under reduced pressure, the residue was neutralized with 1.0 M NH3 in MeOH and purified on silica gel by flash column chromatography (1.0 M NH3 in MeOH/DCM, 1:8) followed by recrystallization from MeOH/Et2O, affording -(3aR,5R,6R,7S,7aR)-7-fluoro-5-(hydroxymethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-6-ol as a white solid (0.093 g, 89%). 1H NMR (400 MHz, CD3OD) δ 6.62 (d, J=6.5 Hz, 1H), 4.89 (td, J=3.5 Hz, 51.0 Hz, 1H), 4.54 (ddd, J=3.5, 6.5, 20.6, 1H), 3.98-3.94 (m, 1H), 3.90-3.84 (m, 1H), 3.83-3.81 (m, 1H), 3.75 (dd, J=5.4, 12.2 Hz, 1H), 2.99 (s, 3H); 13C NMR (100 MHz, CD3OD) δ 90.63 (d, J=181.3 Hz), 88.53 (d, J=2.3 Hz), 73.60 (d, J=4.3 Hz), 66.02 (d, J=17.3 Hz), 64.80-64.50 (m), 62.44, 31.38; MS, (ES, m/z) [M+H]+ 237.1.

Provenance & Evidence