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

HRID 1419485Notes

Reaction equation

HRID 1419485 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].F[C@@H]1[C@H](O)[C@@H](CO)O[C@@H]1OC.[ClH:42]>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:42])[N:17]=[CH:16]2)[C@H:6]1[F:30])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 15736156methyl 2-deoxy-2-fluoro-alpha-D-ribofuranosideHCID 539547511-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-4-diazoacetyl-5-(dimethylaminomethyleneamino)imidazole

Product 1

HCID 538717291-(3,5-di-O-acetyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-4-chloroacetyl-5-(dimethylaminomethyleneamino)imidazoleYield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Compound (37) (80 mg) obtained in item (4) above was dissolved in dichloromethane (4 ml), to which was added at 5° C. a 1.25M hydrogen chloride solution (0.2 ml) in diethylether and the mixture obtained was allowed to undergo the reaction at that temperature overnight. The resulting reaction solution was washed with water, and the organic layer was dried over anhydrous sodium sulfate and then concentrated to give the titled compound (38) (61 mg) as a syrup. Yield: 75%.

Workup

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

Sources & evidence

ORD record
ord-d58d28033bc943369db5903d25deecb6
Source dataset
uspto-grants-1999_03
Patent number
US05886167

Reaction notes

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