Diazomethane → 1-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-diazoacetyl-5-(dimethylaminomethyleneamino)imidazole

HRID 965386Notes

Reaction equation

HRID 965386 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[C:19]([N:20]=[CH:21][N:22]([CH3:24])[CH3:23])=[C:18]([C:25](Cl)=[O:26])[N:17]=[CH:16]2)[C@@H:6]1[F:28])(=[O:3])[CH3:2].[N+:29](=[CH2:31])=[N-:30]>C(OCC)C>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[C:19]([N:20]=[CH:21][N:22]([CH3:24])[CH3:23])=[C:18]([C:25](=[O:26])[CH:31]=[N+:29]=[N-:30])[N:17]=[CH:16]2)[C@@H:6]1[F:28])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 541640981-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-5-(dimethylaminomethyleneamino)imidazole-4-carbonyl chloride

Product 1

HCID 539547491-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-diazoacetyl-5-(dimethylaminomethyleneamino)imidazoleYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The reaction solution containing compound (19) was then added to a 0.2M diazomethane solution (20 ml) in diethylether and the mixture so obtained was allowed to react at room temperature for 1 hour. The resulting reaction solution was filtered and the filtrate was concentrated to give the titled compound (20) (55 mg) as a syrup.

Workup

  1. customthe mixture so obtained
  2. customto react at room temperature for 1 hour
  3. customThe resulting reaction solution
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e74033e4218d428f829c604b3bc9a3ad
Source dataset
uspto-grants-1998_06
Patent number
US05773607

Reaction notes

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