Carbon Dioxide → HCID 178516780, compound

HRID 1419483Notes

Reaction equation

HRID 1419483 reaction equation
NC[C:3]([C:5]1[N:6]=[CH:7][N:8]([C@@H:15]2[O:20][C@H:19]([CH2:21][OH:22])[C@@H:17]([OH:18])[C@H:16]2[F:23])[C:9]=1[N:10]=[CH:11][N:12](C)[CH3:13])=[O:4].C[O-].[Na+].C(=O)=O>CO>[F:23][C@@H:16]1[C@H:17]([OH:18])[C@@H:19]([CH2:21][OH:22])[O:20][C@H:15]1[N:8]1[C:9]2[N:10]=[CH:11][NH:12][CH2:13][C:3](=[O:4])[C:5]=2[N:6]=[CH:7]1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 10942334Sodium MethoxideHCID 537945224-aminoacetyl-1-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-5-(dimethylaminomethyleneamino)imidazole

Product 1

HCID 178516780HCID 178516780, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The compound (24) (20 mg) obtained in item (13) above was dissolved in methanol (0.4 ml), to which was added a 0.2M sodium methylate solution (0.4 ml) in methanol and the resulting mixture was allowed to stand at room temperature overnight. The reaction solution obtained was neutralized with addition of dry ice, then concentrated to leave a residue and the residue was purified by silica gel column chromatography (developer; chloroform-methanol, 4:1), affording the titled compound (25) (6.2 mg) as a colorless solid. Yield: 36%.

Workup

  1. customThe reaction solution obtained
  2. concentrationconcentrated
  3. customto leave a residue
  4. customthe residue was purified by silica gel column chromatography (developer; chloroform-methanol, 4:1)

Sources & evidence

ORD record
ord-9d6120a78bae44259dfc44240380669a
Source dataset
uspto-grants-1999_03
Patent number
US05886167

Reaction notes

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