4-Toluenesulfonyl chloride → HCID 5280128, compound

Participants

Reaction Conditions

Reaction Steps

26 g of 2'-deoxy-5-ethyluridine were dissolved in 400 ml of dry pyridine. The solution was cooled to 0° C. and stirred while 20 g of p-toluenesulfonyl chloride were added portionwise. Stirring at 0° C. was continued for 1 hour and the mixture was then left to stand at 4° C. overnight. The solvent was removed by evaporation and the residue was re-evaporated with toluene. The residue was shaken with 200 ml of methanol and left to stand in a refrigerator for 2.5 hours to give a solid which was removed by filtration, washed with methanol and dried in vacuo to give 18 g of crude product of melting point 183° C. (decomposition). Recrystallization from 450 ml of ethanol gave 13 g of pure 2'-deoxy-5-ethyl-5'-O-(p-toluenesulfonyl)uridine of melting point 189°-190° C. (decomposition).

Provenance & Evidence