Triethyl Phosphate → HCID 86625112, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 100 mg of 3′-azido-thymidine (0.37 mmol) and 0.5 ml triethylphosphate was gradually added to a mixture of 1 ml triethylphosphate and 100 μl phosphorus oxychloride (1.0 mmol) at 0° C. The mixture was maintained at 0-4° C. for 16 h under stirring. Then 10 ml of ice-cold 5% NaHCO3 in water was added and after stirring at 0° C. for 1 hour, the pH was adjusted to 7.0 with NaOH 1M. After further 12 h under stirring, the mixture was extract with 3×10 ml of diethyl ether to remove triethylphosphate. The water solution was subjected to volume reduction (1 ml) and loaded onto a DEAE-cellulose column. The column was eluted with a linear gradient (0.05-0.4 M) of triethylammonium bicarbonate, pH 7.5. Appropriate fractions were evaporated under vacuum. Methanol was added and evaporated again to remove triethylammonium bicarbonate obtaining 3′-azidothymidine-5′-monophosphate triethylammonium salt as white solid (90 mg, 0.15 mmol, yield=40%).

Provenance & Evidence