Acetonitrile → HCID 22981188, compound

HRID 1861976Notes

Reaction equation

HRID 1861976 reaction equation
[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[NH:19][CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(#N)C.[C:37](Cl)(=[O:39])[CH3:38]>C(OCC)(=O)C>[C:24]([O:23][C:21]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[N:19]([C:37](=[O:39])[CH3:38])[CH3:20])=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 22981246HCID 22981246, compound

Product 1

HCID 22981188HCID 22981188, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the compound (540 mg) obtained in Example 446, potassium carbonate (1.96 g) and acetonitrile (30 ml), acetyl chloride(890 mg) was added and heated under reflux for 24 h. Ethyl acetate was added to the reaction mixture, which was washed with water, dried with magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, methylene chloride:ethyl acetate=5:1) to give 330 mg of the titled compound (yield, 55%).

Workup

  1. additionwas added
  2. temperatureheated
  3. temperatureunder reflux for 24 h
  4. washwas washed with water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent, methylene chloride:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-a50a026897444f0f8877c3b8e07cd130
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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