Trifluridine → HCID 131716752, compound

HRID 359887Notes

Reaction equation

HRID 359887 reaction equation
[C@@H:1]1([N:9]2[CH:20]=[C:15]([C:16]([F:19])([F:18])[F:17])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[C:21](Cl)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]>N1C=CC=CC=1>[C:21]([CH:6]([OH:7])[C@H:5]1[O:8][C@@H:1]([N:9]2[CH:20]=[C:15]([C:16]([F:18])([F:17])[F:19])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[CH2:2][C@@H:3]1[OH:4])(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 6256TrifluridineHCID 62493Pivaloyl chloride

Product 1

HCID 131716752HCID 131716752, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a stirring solution of 150 mg of trifluorothymidine in 5 mL of pyridine was added a solution of 90 mg of pivaloyl chloride in 1 ml of pyridine, with cooling. Stirring was continued at room temperature for 10 hours, then the reaction mixture was poured into 20 mL of ice water and extracted with 50 mL of ethyl acetate. The extract was washed with water and dried over sodium sulfate. The ethyl acetate was removed and the residue was purified by silica gel column chromatography using 20:1 chloroform/methanol as eluent. The title compound melted at 130°-132° C. after recrystallization from a mixture of ether and n-hexane.

Workup

  1. temperaturewith cooling
  2. extractionextracted with 50 mL of ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over sodium sulfate
  5. customThe ethyl acetate was removed
  6. customthe residue was purified by silica gel column chromatography
  7. customThe title compound melted at 130°-132° C. after recrystallization
  8. additionfrom a mixture of ether and n-hexane

Sources & evidence

ORD record
ord-c227e6a093bd4b9aa40b7ed9846934ac
Source dataset
uspto-grants-1991_03
Patent number
US05002935

Reaction notes

Loading…