Potassium Hydroxide → HCID 14849578, compound

HRID 728203Notes

Reaction equation

HRID 728203 reaction equation
[OH-].[K+].Cl[CH2:4][C:5]1[O:6][CH:7]=[CH:8][CH:9]=1.[F:10][C:11]1[C:12](=[O:45])[NH:13][C:14](=[O:44])[N:15]([CH:43]=1)[C@@H:16]1[O:42][C@H:20]([CH2:21][O:22]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:18]([OH:19])[CH2:17]1>O1CCOCC1>[F:10][C:11]1[C:12](=[O:45])[NH:13][C:14](=[O:44])[N:15]([CH:43]=1)[C@@H:16]1[O:42][C@H:20]([CH2:21][OH:22])[C@@H:18]([O:19][CH2:4][C:5]2[O:6][CH:7]=[CH:8][CH:9]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2195202-(Chloromethyl)furanHCID 108387042'-deoxy-5'-O-trityl-5-fluorouridine

Product 1

HCID 14849578HCID 14849578, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A 0.35 g quantity of particulate potassium hydroxide and 0.29 g of 2-chloromethylfuran were added to a solution of 1.00 g of 2'-deoxy-5-fluoro-5'-O-trityluridine in 30 ml of dioxane. The mixture was stirred at 80° C. for 2 hours. The solvent was distilled off and the residue was dissolved in 30 ml of ethyl acetate. The solution was washed with water and dried. The residue was dissolved in 15 ml of 80% acetic acid and the solution was left to stand at 80° C. for 2 hours. The solvent was distilled off and the residue was dissolved in ml of ethyl acetate. The solution was washed with water and dried. The residue was treated with chloroform, the insolubles were filtered and recrystallized from ethanol, giving 0.37 g of 2'-deoxy-5-fluoro-3'-O-(2-furanylmethyl)uridine in a yield of 55%.

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in 30 ml of ethyl acetate
  3. washThe solution was washed with water
  4. customdried
  5. dissolutionThe residue was dissolved in 15 ml of 80% acetic acid
  6. waitthe solution was left
  7. waitto stand at 80° C. for 2 hours
  8. distillationThe solvent was distilled off
  9. dissolutionthe residue was dissolved in ml of ethyl acetate
  10. washThe solution was washed with water
  11. customdried
  12. additionThe residue was treated with chloroform
  13. filtrationthe insolubles were filtered
  14. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-738de359e7d241c78c2b1542d1369a45
Source dataset
uspto-grants-1991_09
Patent number
US05047521

Reaction notes

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