Methanol → HCID 86588187, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[2-chloro-6-(4-chloro-2-fluoroanilino)-9H-purin-9-yl]tetrahydrofuran-3-yl acetate (400 mg) in methanol (7 ml), sodium methoxide, 25% in methanol, (3 drops) was added. On stirring for 15 min at 20° C. the reaction mixture went clear. On stirring at 20° C. for a further 90 min a precipitate formed. The precipitate was collected by filtration and dried in vacuo for 16 hours. This was dissolved in a mixture of acetone (15 ml) and 2-2-dimethoxypropane (3 ml), and para-toluene sulphonic acid (193 mg) added. The mixture was stirred at 20° C. for 3 hours. The solvent was removed in vacuo and the residue dissolved in ethyl acetate (50 ml), washed with water (50 ml) and brine (30 ml), dried (MgSO4) and the solvent removed in vacuo. Purification by chromatography on silica gel (Varian Bondelut cartridge), eluting with cyclohexane:ethyl acetate (1:1) gave the title compound as a white foam (240 mg).

Provenance & Evidence