Sodium Hydroxide → HCID 13014291, compound

Participants

Reaction Steps

In a mixture of 10 ml of pyridine and 10 ml of water was dissolved 4 g (0.01 mol) of 1,3-bis(benzoyloxymethyl)-5-fluorouracil. A 5% aqueous caustic soda solution was slowly added dropwise to the solution under agitation while maintaining the pH value of the liquid at 10~11. The mixture was kept for 4 hours at 60° C. whereby alkaline hydrolysis of the starting 1,3-bis(benzoyloxymethyl)-5-fluorouracil was effected. After completion of the hydrolysis reaction, the reaction liquid was concentrated under reduced pressure and cooled. Any remaining unreacted 1,3-bis(benzoyloxymethyl)-5-fluorouracil was then precipitated out and filtered off and the filtrate was subjected to a column chromatographic treatment using a column packed with silica gel. Using a mixture (3:1 in mixing ratio) of benzene and ethyl acetate as eluent, 1-benzoyloxymethyl-5-fluorouracil aimed at was separated as a first elution component. 3-Benzoyloxymethyl-5-fluorouracil formed as by-product was also separated as a second elution component. The yields of 1-benzoyloxymethyl-5-fluorouracil and 3-benzoyloxymethyl-5-fluorouracil were 0.92 g (yield: 35%) and 0.65 g, respectively. After recrystallization from benzene of the crude product, the desired 1-benzoyloxymethyl-5-fluorouracil was obtained as white crystals melting at 179°~180° C.

Provenance & Evidence