Acetic Acid → HCID 54477112, compound

HRID 1981883Notes

Reaction equation

HRID 1981883 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][C@@H:7]([N:20]2[CH:27]=[C:26]([F:28])[C:24](N)=[N:23][C:21]2=[O:22])[C@H:6]1[F:29])(=[O:3])[CH3:2].C(O)(=[O:32])C>>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][C@@H:7]([N:20]2[CH:27]=[C:26]([F:28])[C:24](=[O:32])[NH:23][C:21]2=[O:22])[C@H:6]1[F:29])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 54146905HCID 54146905, compound

Product 1

HCID 54477112HCID 54477112, compound

Procedure

A mixture of 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluorocytosine (650 mg) in 80% acetic acid (50 ml) is heated under reflux for 48 hours. After removal of the solvent in vacuo the residue is chromatographed over a column of silica gel G60 (22×2 cm) using CHCl3 :MeOH (30:1 v/v as the eluent. Each fraction is checked by tlc and the appropriate fractions are collected and evaporated in vacuo, and the residue is crystallized from ethanol to give pure 1-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluorouracil, 300 mg, m.p. 177°-179°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 48 hours
  3. customAfter removal of the solvent in vacuo the residue
  4. customis chromatographed over a column of silica gel G60 (22×2 cm)
  5. customthe appropriate fractions are collected
  6. customevaporated in vacuo
  7. customthe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-78117f4a6a414b748f91f0df3e267152
Source dataset
uspto-grants-1986_06
Patent number
US04594339

Reaction notes

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