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

HRID 965385Notes

Reaction equation

HRID 965385 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.[Cl-:25]>O1CCCC1>[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]([Cl:25])=[O:24])[N:4]=[CH:5]2)[C@@H:8]1[F:21])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 312ChlorideHCID 158583645-amino-1-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)imidazole-4-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (18) (62 mg) obtained in item (8) above was dissolved in tetrahydrofuran (3 ml), to which was then added N,N-dimethylchloroforminium chloride (90 mg) under ice-cooling and the resulting mixture was stirred at the same temperature as above for 30 minutes to effect both the chlorination and N,N-dimethylaminomethylenation reactions. Thus, compound (19) was produced.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-f5440e24239c415fa4c80d705d011ecd
Source dataset
uspto-grants-1998_06
Patent number
US05773607

Reaction notes

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