Hydrochloric Acid → Uridine, 3'-azido-5-chloro-2',3'-dideoxy-

Participants

Reaction Conditions

Reaction Steps

3'-Azido-2',3'-dideoxyuridine (0.25 g; 1 mMol) was dissolved in 2 mL dry dimethylacetamide (DMAC), cooled to 0° C. and 2 mL of 0.5M HCl in DMAC was added. m-Chloroperbenzoic acid (0.277 g; 1.6 mMol) was added in two portions over ten minutes and the mixture was allowed to come to ambient temperature. After two hours, 4 mL H2O was added and the solution filtered. The aqueous DMAC solution was extracted with Et2O (3×3 mL) and the Et2O was evaporated in vacuo to an oil which was applied to a silica gel column. Elution with CHCl3MeOH (15:1 v/v), combination of the appropriate fractions and evaporation in vacuo yielded an oil which was crystallized from Et2O to give 58.5 mg (0.2 mMol, 20%): mp=169°-170° C.

Provenance & Evidence