Pivaloyl chloride → HCID 22240004, compound

HRID 892096Notes

Reaction equation

HRID 892096 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:6](=[O:17])[NH:5][C:4](=[O:18])[C:3]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:27](Cl)(=O)[C:28]([CH3:31])([CH3:30])[CH3:29]>N1C=CC=CC=1>[CH2:20]([N:19]1[C:3]2[C:4](=[O:18])[NH:5][C:6](=[O:17])[N:7]([CH2:8][C:9]3[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)[C:2]=2[N:1]=[C:27]1[C:28]([CH3:31])([CH3:30])[CH3:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 11727890HCID 11727890, compound

Product 1

HCID 22240004HCID 22240004, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound C4 (10.2 g, 29.0 mmol) was dissolved in pyridine (10 mL), to the solution was added pivaloyl chloride (3.50 mL, 30.5 mmol, 1.1 equivalents), and then the mixture was stirred at room temperature for 24 hours. After the reaction solution was concentrated, ethyl acetate was added to the resulting residue, and the deposited solid (7.51 g, 59%) was collected by filtration. The resulting solid was dissolved in 2 mol/L aqueous sodium hydroxide (50 mL), the mixture was refluxed with heating for 1 hour, and the reaction mixture was adjusted to pH 6 with 4 mol/L hydrochloric acid under ice cooling. The deposited solid was collected by filtration and dried under reduced pressure to obtain the title compound (6.61 g, 92%).

Workup

  1. concentrationAfter the reaction solution was concentrated
  2. additionethyl acetate was added to the resulting residue
  3. filtrationthe deposited solid (7.51 g, 59%) was collected by filtration
  4. dissolutionThe resulting solid was dissolved in 2 mol/L aqueous sodium hydroxide (50 mL)
  5. temperaturethe mixture was refluxed
  6. temperaturewith heating for 1 hour
  7. filtrationThe deposited solid was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-2493da2e0c08419687e11b0e6c8f46ad
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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