Ammonia → HCID 69758823, compound

HRID 392322Notes

Reaction equation

HRID 392322 reaction equation
N.C([O:5][C@H:6]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([N:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]([NH2:23])=[NH:22])[C:16]2=[O:24])[O:8][C@@H:7]1[CH2:25][O:26]C(=O)C)(=O)C.[ClH:30]>C(O)(=O)C>[ClH:30].[OH:11][C@@H:10]1[C@H:6]([OH:5])[C@@H:7]([CH2:25][OH:26])[O:8][C@H:9]1[N:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21](=[NH:22])[NH2:23])[C:16]1=[O:24]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 69758690HCID 69758690, compound2×

Product 1

HCID 69758823HCID 69758823, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 5.0 mL of 25% aqueous solution of ammonia was added 0.10 g of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[3-[amino(imino)methyl]-2oxo-1(2H)-pyrazinyl]tetrahydro-3-furanyl acetate at an ice-cooled temperature, and the mixture thus formed was stirred at the same temperature as above for 2 hours. After adding 4.9 mL of acetic acid to the reaction mixture, the solvent was removed under reduced pressure. Further, the same reaction as above was repeated by using 20 mg of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-[3-[amino(imino)methyl]-2-oxo1(2H)-pyrazinyl]tetrahydro-3-furanyl acetate, and the reaction mixture thus obtained was united with the reaction mixture obtained above. The united mixture was purified by reversed phase silica gel column chromatography [eluent: water]. To the solid product thus obtained was added 5.0 mL of 1 mol/L hydrochloric acid, and the solvent was removed under reduced pressure. Further, 5.0 mL of 1 mol/L hydrochloric acid was added and the solvent was removed under reduced pressure. Ethanol was added to the residue thus obtained, and the solid product was collected by filtration to obtain 30 mg of 4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3-oxo-3,4-dihydro-2-pyrazinecarboximidamide hydrochloride as a light yellow-colored solid product.

Workup

  1. temperaturecooled temperature
  2. customthe mixture thus formed
  3. customthe solvent was removed under reduced pressure
  4. customFurther, the same reaction as
  5. customthe reaction mixture thus obtained
  6. customobtained above
  7. customThe united mixture was purified by reversed phase silica gel column chromatography [eluent: water]
  8. customTo the solid product thus obtained
  9. customthe solvent was removed under reduced pressure
  10. additionFurther, 5.0 mL of 1 mol/L hydrochloric acid was added
  11. customthe solvent was removed under reduced pressure
  12. additionEthanol was added to the residue
  13. customthus obtained
  14. filtrationthe solid product was collected by filtration

Sources & evidence

ORD record
ord-315dedf7664c4de284cd6e0a82c642d7
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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