HCID 131719122, compound → HCID 22855931, compound

A solution of the compound of 4'-azidothymidine 5'-monophosphate disodium salt (55 mg, 0.14 mM) in H2O (5 mL) is applied onto a short column of Dowex 50 (H+) resin (8 mL) and eluted with H2O. After concentrating the eluent to 5 mL, tributylamine (32 μL) and pyridine (5 mL) was added and the mixture evaporated in vacuo. The residue was co-evaporated with pyridine then with dimethylformamide. To a solution of the residue in dimethylformamide (1 mL) was added a solution of carbonyldiimidazole (0.11 g, 0.66 mM) in dimethylformamide (1.5 mL). After 20 hours at room temperature, methanol (0.04 mL, 1.0 mM) was added. Thirty minutes later a solution of tributylammonium pyrophosphate (0.675 mM) in dimethylformamide (7 mL) was added and mixture was vigorously stirred for 20 hours at room temperature. After filtration, the solution was diluted with an equal volume of methanol and evaporated to a sirup. The sirup was dissolved in water (10 mL) and applied onto a 3×23 cm column of DEAE Sephadex (carbonate form) which was eluted with a linear gradient consisting of 2 L of water and 2 L of 0.5M triethylammonium bicarbonate (pH 7). The 4'-azidothymidine 5'-diphosphate was eluted pure followed by the 4'-azidothymidine 5-'triphosphate. After evaporation of solvent and repeated co-evaporation with water, each product was dissolved in a small amount of methanol. The addition of a 0.45M solution of sodium perchlorate in acetone then precipitated the sodium salts. Filtering off the precipitates and drying in vacuo gave 4'-azidothymidine 5'-diphosphate trisodium salt (12 mg) and 4'-azidothymidine 5'-triphosphate tetrasodium salt (54 mg, mp 204° C., decomposition).

1. washeluted with H2O
2. concentrationAfter concentrating the eluent to 5 mL, tributylamine (32 μL) and pyridine (5 mL)
3. additionwas added
4. customthe mixture evaporated in vacuo
5. additionTo a solution of the residue in dimethylformamide (1 mL) was added a solution of carbonyldiimidazole (0.11 g, 0.66 mM) in dimethylformamide (1.5 mL)
6. additionmethanol (0.04 mL, 1.0 mM) was added
7. additionThirty minutes later a solution of tributylammonium pyrophosphate (0.675 mM) in dimethylformamide (7 mL) was added
8. filtrationAfter filtration
9. additionthe solution was diluted with an equal volume of methanol
10. customevaporated to a sirup
11. dissolutionThe sirup was dissolved in water (10 mL)
12. washwas eluted with a linear gradient
13. washThe 4'-azidothymidine 5'-diphosphate was eluted pure
14. customAfter evaporation of solvent
15. dissolutioneach product was dissolved in a small amount of methanol
16. additionThe addition of a 0.45M solution of sodium perchlorate in acetone
17. customthen precipitated the sodium salts
18. filtrationFiltering off the
19. customprecipitates
20. customdrying in vacuo

ORD record

ord-fd71f511e29d4565b301d961cb979206

Source dataset

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05449664