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

HRID 1419472Notes

Reaction equation

HRID 1419472 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](=[O:28])[CH2:26]Cl)[N:17]=[CH:16]2)[C@@H:6]1[F:29])(=[O:3])[CH3:2].[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C)C=O>[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:28])[CH2:26][N:30]=[N+:31]=[N-:32])[N:17]=[CH:16]2)[C@@H:6]1[F:29])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 538717281-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-chloroacetyl-5-(dimethylaminomethyleneamino)imidazole2×

Product 1

HCID 542783081-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-azidoacetyl-5-(dimethylaminomethyleneamino)imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In step 15, compound (21) is reacted with sodium azide in N,N-dimethylformamide at room temperature for converting the chloro group of compound (21) into azido group, whereby 1-(3,5-di-O-acetyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)-4-azidoacetyl-5-(dimethylaminomethyleneamino)imidazole [compound (22)] is produced.

Sources & evidence

ORD record
ord-2499041e93514a4e9d5405f1bc29b2f5
Source dataset
uspto-grants-1999_03
Patent number
US05886167

Reaction notes

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