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

HRID 1419479
Notes
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Reaction equation

HRID 1419479 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]>ClCCl.C(OCC)C>[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 539547491-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-diazoacetyl-5-(dimethylaminomethyleneamino)imidazole

Product 1

HCID 538717281-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)-4-chloroacetyl-5-(dimethylaminomethyleneamino)imidazoleYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

The compound (20) (21.8 mg) obtained in item (9) above was dissolved in dichloromethane (1 ml), and to the resulting solution was added a 1.25M hydrogen chloride solution (0.05 ml) in diethylether at 5° C., and the mixture so obtained was allowed to stand at that temperature overnight. The resulting reaction solution was washed with water and the organic layer obtained was dried over anhydrous sodium sulfate and concentrated to give the titled compound (21) (18.0 mg) as a syrup. Yield: 81%.

Workup

  1. customthe mixture so obtained
  2. customto stand at that temperature overnight
  3. customThe resulting reaction solution
  4. washwas washed with water
  5. customthe organic layer obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7404b42a76dd440db9b9a76783fdef6b
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05886167

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes