Sodium Carbonate → HCID 57016808, compound

Participants

Reaction Steps

(3R,4S,5S,6R)-2-Bromo-5,6-dichloro-1-(4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-3-yl)-1H-benzimidazole (part e of this example, 0.810 g, 1.53 mmol) was dissolved in 1:1 methanol-ethanol (100 ML) and treated with a solution of sodium carbonate (0.163 g, 1.53 mmol) in water (10 ML). After 0.5 h at room temperature, TLC analysis indicated a single new spot (silica gel, 10% methanol-chloroform). The pH was then adjusted to 5 with glacial acetic acid and the solvents evaporated in vacuo. The residual solid was slurried in water until the solids were free-flowing, then suction-filtered and dried overnight in vacuo affording the title compound as a white solid (0.510 g, 81%); m.p. 207-209° C.; [α]20D−162° (c 0.26, EtOH); 1H-NMR (DMSO-d6, 200 MHz) δ: 8.30, 8.28 (s, each 1H), 5.26 (d, J=5.5 Hz, 1H), 5.13 (d, J=4.2 Hz, 1H), 5.05 (t, J=4.7 Hz, 1H), 5.04 (m, 1H), 4.78 (m, 1H), 4.33-4.00 (m, 3H), 3.84-3.68 (m, 3H).

Provenance & Evidence