Trifluridine → HCID 13387398, compound

HRID 1655486Notes

Reaction equation

HRID 1655486 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH:16]=1)[C@@H:8]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]1.C(N(CC)CC)C.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC(N(C)C)=O>[C:28]([N:5]1[C:4](=[O:18])[C:3]([C:2]([F:1])([F:19])[F:20])=[CH:16][N:7]([C@@H:8]2[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[CH2:9]2)[C:6]1=[O:17])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 6256TrifluridineHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 13387398HCID 13387398, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

12 Grams of 2'-deoxy-5-trifluoromethyluridine was dissolved in 30 ml of dimethylacetamide. Thereto was added 8 ml of triethylamine, and further to the mixture being cooled with ice-water was added 5.6 g of benzoyl chloride. The whole mixture was stirred overnight. The reaction mixture was subjected to filtration, the resulting filtrate was subjected to evaporation and the residue was dissolved in ether. To the ether solution being stirred was slowly added water. The resulting precipitate was collected by filtration. The precipitate collected was recrystallized from ether-petroleum ether. The yield was 8.0 g. M.p. 144.5° to 146° C.

Workup

  1. filtrationThe reaction mixture was subjected to filtration
  2. customthe resulting filtrate was subjected to evaporation
  3. dissolutionthe residue was dissolved in ether
  4. stirringTo the ether solution being stirred
  5. filtrationThe resulting precipitate was collected by filtration
  6. customThe precipitate collected
  7. customwas recrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-ef679ace28754b27bc898e8d152f2f6c
Source dataset
uspto-grants-1993_10
Patent number
US05250673

Reaction notes

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