Trifluridine → HCID 14722783, compound

HRID 1655487Notes

Reaction equation

HRID 1655487 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.Cl[CH:29]1[CH2:33][CH2:32][CH2:31][O:30]1.C(Cl)(Cl)Cl.C(O)C>CC(N(C)C)=O>[O:30]1[CH2:31][CH2:32][CH2:33][CH:29]1[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]

Participants

6

Reactant 4

HCID 6256TrifluridineHCID 8471TriethylamineHCID 178730Furan, 2-chlorotetrahydro-HCID 21889567Chloroform ethanol

Product 1

HCID 14722783HCID 14722783, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

5.92 Grams of 2'-deoxy-5-trifluoromethyluridine was dissolved in 40 ml of dry dimethylacetamide. Thereto was added 2.23 g of triethylamine and the mixture was ice-cooled. Thereto was added dropwise a dry dimethylacetamide solution containing 2.34 g of 2-chlorotetrahydrofuran prepared just prior to use, and the mixture was stirred overnight. The reaction mixture was subjected to filtration and the resulting filtrate was subjected to evaporation. The residue was extracted with chloroform and the extract was dried with anhydrous sodium sulfate. The solvent in the extract was removed by evaporation to obtain an oily residue. The residue was treated by a silica gel column chromatography (developing solvent: chloroform/ethanol =20/1). The eluate was recrystallized from ethanol-petroleum ether to obtain 2.80 g of the desired product. Melting point: 127°-128° C.

Workup

  1. temperaturecooled
  2. customprepared just
  3. filtrationThe reaction mixture was subjected to filtration
  4. customthe resulting filtrate was subjected to evaporation
  5. extractionThe residue was extracted with chloroform
  6. dry with materialthe extract was dried with anhydrous sodium sulfate
  7. customThe solvent in the extract was removed by evaporation
  8. customto obtain an oily residue
  9. customThe eluate was recrystallized from ethanol-petroleum ether

Sources & evidence

ORD record
ord-4e80b9fc67ce4941bd99e2098a4fcb89
Source dataset
uspto-grants-1993_10
Patent number
US05250673

Reaction notes

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