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

HRID 965392Notes

Reaction equation

HRID 965392 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:15][C@H:14]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]2[F:21])[CH:5]=[N:4][C:3]=1[C:22]([OH:24])=O.F[C@@H]1[C@H](O)[C@@H](CO)OC1O.[Cl-].[N+:36](=[CH2:38])=[N-:37]>O1CCCC1.C(OCC)C>[C:11]([O:10][C@@H:9]1[C@@H:14]([CH2:16][O:17][C:18](=[O:20])[CH3:19])[O:15][C@@H:7]([N:6]2[C:2]([N:1]=[CH:5][N:6]([CH3:7])[CH3:2])=[C:3]([C:22](=[O:24])[CH:38]=[N+:36]=[N-:37])[N:4]=[CH:5]2)[C@H:8]1[F:21])(=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 312ChlorideHCID 9550DiazomethaneHCID 15858348GlyTouCan:G86674LVHCID 541707655-amino-1-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)imidazole-4-carboxylic acid

Product 1

HCID 539547511-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-4-diazoacetyl-5-(dimethylaminomethyleneamino)imidazoleYield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound (35) (93 mg) obtained in item (3) above was dissolved in tetrahydrofuran (4.5 ml), to which was then added N,N-dimethylchloroforminium chloride (135 mg) under ice-cooling. The resulting mixture was allowed to undergo the reaction for 30 minutes. The reaction solution containing compound (36) thus produced was then added to a 0.2M diazomethane solution (30 ml) in diethylether and the reaction was maintained at room temperature for 1 hour. The reaction solution so obtained was filtered and the filtrate was concentrated to give the titled compound (37) (83 mg) as a syrup. Yield: 75%.

Workup

  1. temperaturecooling
  2. customthe reaction for 30 minutes
  3. customthus produced
  4. customThe reaction solution so obtained
  5. filtrationwas filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2712ac3b83004f3ead1fe3bc4254938f
Source dataset
uspto-grants-1998_06
Patent number
US05773607

Reaction notes

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