Potassium Acetate → 3'-Fluorothymidine

To a solution of 3.22 g (10 millimoles) 3'-deoxy-3'-fluoro-5'-mesylthymidine in 10 ml N,N-dimethylformamide, was added 1.96 g (20 millimoles) potassium acetate, and the mixture was heated at 110°±5° C. for 60 minutes with stirring. The solvent was distilled off from the reaction mixture under reduced pressure, 30 ml water was added to the residue, and the mixture was extracted twice with 50 ml ethyl acetate. The extract was washed twice with 30 ml water and dried over anhydrous sodium sulfate, the solvent was distilled off from the dried extract under reduced pressure, and the residue was dissolved in methanol. This solution was decolorized by treatment with 1.4 g of activated charcoal, the decolorized solution obtained by filtering off the charcoal was concentrated, and the residue was treated with ammonia-saturated methanol and subjected to purification in the same way as in Example 1, giving 1.8 g (7.38 millimoles) of 3'-deoxy-3'-fluorothymidine as white, granular crystals. The yield was 73.8%.

1. temperaturethe mixture was heated at 110°±5° C. for 60 minutes
2. distillationThe solvent was distilled off from the reaction mixture under reduced pressure, 30 ml water
3. additionwas added to the residue
4. extractionthe mixture was extracted twice with 50 ml ethyl acetate
5. washThe extract was washed twice with 30 ml water
6. dry with materialdried over anhydrous sodium sulfate
7. distillationthe solvent was distilled off from the dried
8. extractionextract under reduced pressure
9. dissolutionthe residue was dissolved in methanol
10. customthe decolorized solution obtained
11. filtrationby filtering off the charcoal
12. concentrationwas concentrated
13. additionthe residue was treated with ammonia-saturated methanol
14. customsubjected to purification in the same way as in Example 1

ORD record

ord-907a78d54bf041ec8689ae7dd34676b5

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05166327