Potassium Hydroxide → HCID 14849578, compound

HRID 981727Notes

Reaction equation

HRID 981727 reaction equation
[F:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:35])[N:6]([CH:34]=1)[C@@H:7]1[O:33][C@H:11]([CH2:12][O:13]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C@@H:9]([OH:10])[CH2:8]1.[OH-].[K+].[CH2:39](Cl)[C:40]1[O:44][CH:43]=[CH:42][CH:41]=1>O1CCOCC1>[F:1][C:2]1[C:3](=[O:36])[NH:4][C:5](=[O:35])[N:6]([CH:34]=1)[C@@H:7]1[O:33][C@H:11]([CH2:12][OH:13])[C@@H:9]([O:10][CH2:39][C:40]2[O:44][CH:43]=[CH:42][CH:41]=2)[CH2:8]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

To a solution of 1.00 g of 2'-deoxy-5-fluoro-5'-O-trityluridine in 30 ml cf dioxane were added 0.35 g of finely divided powder of potassium hydroxide and 0.29 g of furfuryl chloride, and the mixture was stirred at 80° C. for 2 hours. The solvent was evaporated off and the residue was dissolved in 30 ml of ethyl acetate The solution was washed with water, dried and concentrated. 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 evaporated off and the residue was dissolved in 30 ml of ethyl acetate, and the solution was washed with water, dried and concentrated. The residue was treated with chloroform and the insoluble matters were filtered and recrystallized from ethanol, thereby giving 0.37 g of 2'- deoxy-5 fluoro-3'-O-furfuryluridine.

Workup

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

Sources & evidence

ORD record
ord-04d7ecc48d3842cfaa4a05ae383113ed
Source dataset
uspto-grants-1991_02
Patent number
US04992534

Reaction notes

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