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

HRID 965377Notes

Reaction equation

HRID 965377 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:29])[CH:26]=[N+]=[N-])[N:17]=[CH:16]2)[C@@H:6]1[F:30])(=[O:3])[CH3:2].[ClH:31].C(OCC)C>ClCCl>[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:29])[CH2:26][Cl:31])[N:17]=[CH:16]2)[C@@H:6]1[F:30])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 539547491-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-diazoacetyl-5-(dimethylaminomethyleneamino)imidazole2×

Product 1

HCID 538717281-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-chloroacetyl-5-(dimethylaminomethyleneamino)imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In step 14, compound (20) is reacted in dichloromethane with hydrogen chloride in the form of a diethylether solution under ice-cooling, to convert the 4-diazoacetyl group of compound (20) into 4-chloroacetyl group. Thereby, 1-(3,5-di-O-acetyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)-4-chloroacetyl-5-(dimethylaminomethyleneamino)imidazole [compound (21)] is produced.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-2dd51530c9aa4bfeb439b408083a46d2
Source dataset
uspto-grants-1998_06
Patent number
US05773607

Reaction notes

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