Floxuridine → 2'-deoxy-5'-O-trityl-5-fluorouridine

HRID 728615Notes

Reaction equation

HRID 728615 reaction equation
[F:1][C:2]1[C:3](=[O:17])[NH:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.[C:18](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:18]([O:13][CH2:12][C@H:11]1[O:14][C@@H:7]([N:6]2[CH:15]=[C:2]([F:1])[C:3](=[O:17])[NH:4][C:5]2=[O:16])[CH2:8][C@@H:9]1[OH:10])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 5790FloxuridineHCID 6456Trityl chloride

Product 1

HCID 108387042'-deoxy-5'-O-trityl-5-fluorouridineYield 56.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 2.5 ml of pyridine were dissolved 0.25 g of 2'-deoxy-5-fluorouridine and 0.34 g of trityl chloride, and the solution was reacted at 60° C. for 4 hours under stirring. After completion of the reaction, the reaction mixture was poured into 80 ml of ice-cold water and precipitated crystals were collected by filtration. These crystals were dissolved in 30 ml of ethyl acetate, washed with saturated saline solution, dried over anhydrous magensium sulfate and condensed under reduced pressure. The residue obtained was applied to silica gel column chromatography to give 0.28 g (Yield: 56%) of the title compound.

Workup

  1. customthe solution was reacted at 60° C. for 4 hours
  2. customAfter completion of the reaction
  3. customprecipitated crystals
  4. filtrationwere collected by filtration
  5. dissolutionThese crystals were dissolved in 30 ml of ethyl acetate
  6. washwashed with saturated saline solution
  7. dry with materialdried over anhydrous magensium sulfate and condensed under reduced pressure
  8. customThe residue obtained

Sources & evidence

ORD record
ord-189534b91cef4a5492448666057c3cad
Source dataset
uspto-grants-1991_09
Patent number
US05049551

Reaction notes

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