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

HRID 965375Notes

Reaction equation

HRID 965375 reaction equation
[Cl-:1].[NH2:2][C:3]1[N:7]([C@@H:8]2[O:16][C@H:15]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]2[F:22])[CH:6]=[N:5][C:4]=1[C:23]([OH:25])=O>O1CCCC1>[C:12]([O:11][C@@H:10]1[C@@H:15]([CH2:17][O:18][C:19](=[O:21])[CH3:20])[O:16][C@@H:8]([N:7]2[C:3]([N:2]=[CH:6][N:7]([CH3:8])[CH3:3])=[C:4]([C:23]([Cl:1])=[O:25])[N:5]=[CH:6]2)[C@@H:9]1[F:22])(=[O:14])[CH3:13]

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

In step 12, compound (18) is dissolved in tetrahydrofuran and reacted with N,N-dimethylchloroforminium chloride under ice-cooling, whereby 1-(3,5-di-O-acetyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)-5-(dimethylaminomethyleneamino)imidazole-4-carbonyl chloride [compound (19)] is produced.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-9c50216a68a34a87a111e97c8883e573
Source dataset
uspto-grants-1998_06
Patent number
US05773607

Reaction notes

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