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

HRID 965376Notes

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: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

Reactant 2

HCID 9550Diazomethane

HCID 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)imidazole

Procedure

In step 13, compound (19) is reacted with diazomethane at room temperature without being separated from the reaction solution, so that the 4-chlorocarbonyl group of compound (19) is converted into diazoacetyl group, affording 1-(3,5-di-O-acetyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)-4-diazoacetyl-5-(dimethylaminomethyleneamino)imidazole [compound (20)].

Workup

customwithout being separated from the reaction solution, so that the 4-chlorocarbonyl group of compound (19)

Sources & evidence

ORD record: ord-2462913cc2c945748955a9820698d02f
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773607

Reaction notes

Loading…