Water → HCID 69758690, compound

HRID 392321Notes

Reaction equation

HRID 392321 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[CH:5][N:4]=[C:3]1[C:8](=[NH:10])[NH2:9].C(O[C@@H:15]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:16]1[O:17][C:18](=[O:20])[CH3:19])(=O)C.FC(F)(F)C(O)=O.O>C[Si](C)(C)N[Si](C)(C)C.C(#N)C.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>[C:23]([O:22][C@H:21]1[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:15]([N:7]2[CH:6]=[CH:5][N:4]=[C:3]([C:8]([NH2:9])=[NH:10])[C:2]2=[O:1])[O:27][C@@H:26]1[CH2:28][O:29][C:30](=[O:32])[CH3:31])(=[O:25])[CH3:24]

Participants

8

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 135674105HCID 135674105, compound2×

Product 1

HCID 69758690HCID 69758690, compoundYield 59.4%

Reagents, catalysts & solvents 3

HCID 6097028Ammonium SulfateCatalyst2×HCID 6342AcetonitrileSolventHCID 13838HexamethyldisilazaneSolvent

Procedure

In 2.0 mL of 1,1,1,3,3,3-hexamethyldisilazane were suspended 0.20 g of 3-oxo-3,4-dihydro-2-pyrazinecarboximidamide and 10 mg of ammonium sulfate. Under a stream of nitrogen gas, the suspension was heated under reflux for 10 minutes. After adding 9.0 mg of ammonium sulfate, the mixture was heated under reflux for an additional 2 hours. The reaction mixture was allowed to cool, and the solvent was removed under reduced pressure. The residue thus obtained was dissolved in 4.0 mL of acetonitrile, 0.46 g of β-D-ribofuranose-1,2,3,5-tetraacetate and 0.34 mL of stannic (IV) chloride were successively added, and the mixture thus obtained was stirred at room temperature for 3 hours. Then, 10 μL of trifluoroacetic acid and 1.0 mL of water were added to the reaction mixture, and the solvent was removed under reduced pressure. Further, the same reaction as above was repeated by using 0.05 g of 3-oxo-3,4-dihydro-2-pyrazinecarboximidamide. The reaction mixture thus obtained was united with the reaction mixture obtained above, and the product was purified by reversed phase silica gel column chromatography [eluent: acetonitrile:water=1:4] to obtain 0.34 g of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[3-[amino(imino)methyl]-2-oxo-1(2H)-pyrazinyl]tetrahydro-3-furanyl acetate as a light yellow-colored solid product.

Workup

  1. temperatureUnder a stream of nitrogen gas, the suspension was heated
  2. temperatureunder reflux for 10 minutes
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for an additional 2 hours
  5. temperatureto cool
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customthe mixture thus obtained
  9. customthe solvent was removed under reduced pressure
  10. customFurther, the same reaction as
  11. customThe reaction mixture thus obtained
  12. customobtained above, and the product
  13. customwas purified by reversed phase silica gel column chromatography [eluent: acetonitrile:water=1:4]

Sources & evidence

ORD record
ord-fb204338f153454280229a0bdd4e0b6e
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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