Acetic Acid → HCID 67177835, compound

Participants

Reaction Steps

Chlorine gas was bubbled slowly into a suspension of 5-chloro-3′-fluoro-2′,3′-dideoxyuridine (75 mg, 0.28 mmol) in glacial acetic acid (5 ml) at 25° C. with stirring until the light yellow-green color of the resulting solution persisted. The reaction was allowed to proceed for 30 min. at 25° C., prior to evaporation. Purification of the residue obtained by PTLC using ethylacetate:hexanes (3:7, v/v) as development solvent afforded diastereomer (6S)-5,5-dichloro-O6-5′-cyclo-5,6-dihydro-3′-fluoro-2′,3′-dideoxyuridine (R-31) and one, diastereomer of 5,5-dichloro-6-acetoxy-5,6-dihydro-3′-fluoro-2′,3′-dideoxyuridine.

Provenance & Evidence