Sodium Hydroxide → HCID 13014291, compound

HRID 2286695Notes

Reaction equation

HRID 2286695 reaction equation
C(OC[N:11]1[CH:18]=[C:17]([F:19])[C:15](=[O:16])[N:14]([CH2:20][O:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:12]1=[O:13])(=O)C1C=CC=CC=1.[OH-].[Na+]>N1C=CC=CC=1.O>[C:22]([O:21][CH2:20][N:14]1[C:15](=[O:16])[C:17]([F:19])=[CH:18][NH:11][C:12]1=[O:13])(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13014282HCID 13014282, compound2×

Product 1

HCID 13014291HCID 13014291, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

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.

Workup

  1. temperaturewhile maintaining the pH value of the liquid at 10~11
  2. customAfter completion of the hydrolysis reaction
  3. customthe reaction liquid
  4. concentrationwas concentrated under reduced pressure
  5. temperaturecooled
  6. customAny remaining unreacted 1,3-bis(benzoyloxymethyl)-5-fluorouracil was then precipitated out
  7. filtrationfiltered off
  8. customat was separated as a first elution component

Sources & evidence

ORD record
ord-026c15ef99614a769a1d36ab6542ee15
Source dataset
uspto-grants-1981_05
Patent number
US04267326

Reaction notes

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