Acetic Acid → HCID 18336830, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (3aR,4S,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-N-(2-hydroxypropyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide (6.60 g) and powdered 4 Å molecular sieves (10 g) in dichloromethane (165 ml) at 0° C., was added acetic acid (3.0 ml) followed by the portionwise addition of pyridinium dichromate (9.36 g). The mixture was stirred at 0° C. for 15 min and then at 20° C. for 2 hours. Isopropanol (10 ml) was added and the mixture stirred for 15 min. Silica gel (Merck 9385, 9.9 g) and ethyl acetate (165 ml) were added and the reaction stirred for a further 15 min. The mixture was filtered through celite and the filter cake washed with ethyl acetate (300 ml). The filtrate was evaporated in vacuo to give a brown solid. Purification by flash chromatography on silica gel, eluting with dichloromethane:methanol (100:3) gave a light brown foam. Further purification by chromatography on silica gel (Merck 9385), eluting with ethyl acetate followed by ethyl acetate:methanol (100:2) gave the title compound as a white foam (4.6 g).

Provenance & Evidence