Toluene → N4-palmityloxycarbonylarabinofuranosylcytosine

Participants

Reaction Steps

A toluene solution containing 1.8 g of palmityloxycarbonyl chloride is added to 20 ml of a dimethylacetamide solution containing 1.5 g of arabinofuranosylcytosine and 1.7 g of sodium hydrogen carbonate. The reaction is carried out at room temperature with stirring of the mixture for 3 hours. After the reaction is completed, the reaction mixture is poured into an ice-water and the precipitated solids are collected by filtration, followed by washing successively with acetone and with hot chloroform. The resultant solids are dissolved in a mixture of chloroform-methanol and then subjected once to filtration, followed by removal of the solvent. The residue is subjected to crystallization from n-hexane to give 0.92 g of N4 -palmityloxycarbonylarabinofuranosylcytosine (Yield:30%).

Provenance & Evidence