tert-Butanol → Tri-O-acetylguanosine

HRID 2184176Notes

Reaction equation

HRID 2184176 reaction equation
[C@@H:1]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].C[C:22]([OH:25])([CH3:24])C>CN(C=O)C.CC(OC(C)=O)=O.N1C=CC=CC=1>[C:2]([O:3][C@@H:2]1[C@H:4]([O:5][C:4](=[O:5])[CH3:6])[C@@H:6]([CH2:7][O:8][C:22](=[O:25])[CH3:24])[O:9][C@H:1]1[N:10]1[C:20]2[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=2[N:12]=[CH:11]1)(=[O:3])[CH3:1]

Participants

6

Reactant 2

HCID 6386tert-ButanolHCID 135398635Guanosine

Product 1

HCID 135465084Tri-O-acetylguanosine

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a suspension of guanosine (1) (Dried in vacuo over P2O5 for 2 days at 100°, 10.6 g, 37.6 mmole) in DMF (distilled from P2O5,30 ml), Ac2O (re-distilled, 22.4 ml) and pyridine (distilled from KOH, 11.2 ml) were added. The mixture was heated with stirring at 75°. The mixture became clear solution after 1.5 h. Heating was continued for another 2.5 h. The resulting clear solution is filtered while hot, cooled to temperature, and evaporated in vacuo to afford a heavy, crystalline suspension. A portion (35 ml) of 2-methyl-2-propanol was added. The suspension is filtered, and the filter cake was washed with 2-methyl-2-propanol and dried. This crystalline is the hemi-solvate with HCONMe2, and was added to boiling 2-methyl-2-propanol, and the suspension was boiled under reflux for 5 min, cooled and refrigerated for 10 h at −5°. After filtration, the white crystalline was dried in air overnight, dried in vacuo over P2O5 for 2 days at 80°, to give white powder (12.0 g, 78.4%, mp:227-230°, lit. 226-231°).

Workup

  1. additionwere added
  2. temperatureThe mixture was heated
  3. customafter 1.5 h
  4. temperatureHeating
  5. filtrationThe resulting clear solution is filtered while hot,
  6. temperaturecooled to temperature
  7. customevaporated in vacuo
  8. customto afford a heavy, crystalline suspension
  9. filtrationThe suspension is filtered
  10. washthe filter cake was washed with 2-methyl-2-propanol
  11. customdried
  12. additionwas added
  13. temperatureunder reflux for 5 min
  14. temperaturecooled
  15. waitrefrigerated for 10 h at −5°
  16. filtrationAfter filtration
  17. customthe white crystalline was dried in air overnight
  18. dry with materialdried in vacuo over P2O5 for 2 days at 80°
  19. customto give white powder (12.0 g, 78.4%, mp:227-230°, lit. 226-231°)

Sources & evidence

ORD record
ord-42aad3c0b6d74308b5a824b9216c39a3
Source dataset
uspto-grants-2005_05
Patent number
US06900315B2

Reaction notes

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