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

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Reaction Steps

3'-Azido-2'-deoxyuridine (0.25 g; 1 mMol) was dissolved in 2 mL dry dimethylacetamide (DMAC), cooled to 0° 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 CHCl3 /MeoH (15:1 v/v), combination of 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.; UV (nm): at pH 1 max=276 (=7400), min=239 (=500); at pH 13 max=274 (=6400), min=249 (=3800); H1NMR (DMSO-d6) 8.29 (s, 1H, H6), 6.05 (t,1H,H1', J=5.5 Hz), 5.49-5.29 (m,1H,5'-OH), 4.44-4.20 (m,1H,H3'), 3.88-3.71 (m,1H,H4'), 3.71-3.53 (m,2H,H5'), 2.63-2.31 (m,2H,H2'); analysis calculated for C9H10N5O4Cl:ε37.58, H 3.50, N 24.35, Cl 12.32.

Provenance & Evidence