Acetic Anhydride → HCID 54381255, compound

HRID 1109361Notes

Reaction equation

HRID 1109361 reaction equation
[OH:1][N:2]([CH3:27])[C:3]([N:5]1[CH2:9][CH2:8][C:7](=[CH:10][C:11]2[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:14]([OH:21])=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:12]=2)[C:6]1=[O:26])=[O:4].[C:28](OC(=O)C)(=[O:30])[CH3:29]>N1C=CC=CC=1>[C:28]([O:1][N:2]([CH3:27])[C:3]([N:5]1[CH2:9][CH2:8][C:7](=[CH:10][C:11]2[CH:16]=[C:15]([C:17]([CH3:19])([CH3:18])[CH3:20])[C:14]([OH:21])=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:12]=2)[C:6]1=[O:26])=[O:4])(=[O:30])[CH3:29]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54378503HCID 54378503, compound

Product 1

HCID 54381255HCID 54381255, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-(N-hydroxy-N-methylcarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one (Ia-6) (222 mg, 0.6 mmole) dissolved into pyridine (3 ml), 1.8 ml of acetic anhydride was added and the mixture was stirred at room temperature for 5 hours, then the resulting mixture was evaporated. Hydrochloric acid (0.5N) was added thereto, and the mixture was subjected to extraction with dichloromethane. The organic layer was washed with water, sodium bicarbonate, and water in order, dried over magnesium sulfate, and evaporated. The obtained residue was recrystallized from dichloromethane/ether, whereby 211 mg of the objective compound (Ia-16) was obtained in 84% yield.

Workup

  1. additionwas added
  2. customthe resulting mixture was evaporated
  3. additionHydrochloric acid (0.5N) was added
  4. extractionthe mixture was subjected to extraction with dichloromethane
  5. washThe organic layer was washed with water, sodium bicarbonate, and water in order
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe obtained residue was recrystallized from dichloromethane/ether

Sources & evidence

ORD record
ord-4a22426d886249c3af3ea1ceb6d0ecd5
Source dataset
uspto-grants-1994_06
Patent number
US05319099

Reaction notes

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