Acetic Anhydride → HCID 54726179, compound

HRID 1657357Notes

Reaction equation

HRID 1657357 reaction equation
[OH:1][C:2]1[C:3]([C@@H:10]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]2[OH:12])=[N:4][NH:5][C:6]=1[C:7]([NH2:9])=[O:8].[C:19](OC(=O)C)(=[O:21])[CH3:20]>CO>[OH:1][C:2]1[C:3]([C@@H:10]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:13]([OH:14])[C@H:11]2[OH:12])=[N:4][N:5]([C:19](=[O:21])[CH3:20])[C:6]=1[C:7]([NH2:9])=[O:8]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 135413551Pyrazofurin

Product 1

HCID 54726179HCID 54726179, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.0 g. of 4-hydroxy-3-β-D-ribofuranosylpyrazole-5-carboxamide in 20 cc. of anhydrous methyl alcohol was stirred and cooled to 0°C. To the cold stirred solution was added 5 cc. of acetic anhydride dropwise over about 10 minutes. The reaction mixture was stirred for about 1 hour while the temperature was allowed to increase to about 25°C. The solvent was removed under reduced pressure to provide an oily residue which was dissolved in 25 cc. of 50 percent methanol-toluene. Again the solvent was removed under reduced pressure. This procedure was repeated three times to insure complete removal of any excess acylating agent. After the final solvents were totally removed, 4-hydroxy-3β-D-ribofuranosyl-N1 -acetylpyrazole-5-carboxamide remained as a white solid.

Workup

  1. additionTo the cold stirred solution was added 5 cc
  2. temperatureto increase to about 25°C
  3. customThe solvent was removed under reduced pressure
  4. customto provide an oily residue which
  5. dissolutionwas dissolved in 25 cc
  6. customAgain the solvent was removed under reduced pressure
  7. customremoval of any excess acylating agent
  8. customAfter the final solvents were totally removed

Sources & evidence

ORD record
ord-702965488f124ff09070e24035941d64
Source dataset
uspto-grants-1976_06
Patent number
US03960836

Reaction notes

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