Potassium Hydroxide → 2-(3-{[(Tert-butyl)oxycarbonyl]methyl}-2-oxoimidazolidinyl)acetic acid
Reaction equation
C([O:5][C:6]([CH2:8][N:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]1=[O:22])=[O:7])(C)(C)C.[OH-].[K+]>C(O)C.O>[C:18]([O:17][C:15]([CH2:14][N:11]1[CH2:12][CH2:13][N:9]([CH2:8][C:6]([OH:7])=[O:5])[C:10]1=[O:22])=[O:16])([CH3:21])([CH3:19])[CH3:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a solution of tert-butyl 2-(3-{[(tert-butyl)oxycarbonyl]methyl}-2-oxoimidazolidinyl)acetate (1.14 g) in ethanol (10 ml) and water (10 ml) was added potassium hydroxide (0.22 g) and then the reaction mixture stirred at 70° C. for 5 hours. After the ethanol was removed under reduced pressure, to the residue was added saturated aqueous sodium hydrogen carbonate solution. The aqueous phase was washed with ethyl acetate, acidified with 10% hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and evaporated under reduced pressure. The precipitate was recrystallized with ethyl acetate and filtered off to give 2-(3-{[(tert-butyl)oxycarbonyl]methyl}-2-oxoimidazolidinyl)acetic acid (0.30 g) as a colorless solid.
Workup
- customAfter the ethanol was removed under reduced pressure, to the residue
- additionwas added saturated aqueous sodium hydrogen carbonate solution
- washThe aqueous phase was washed with ethyl acetate
- extractionextracted with ethyl acetate
- dry with materialThe organic phase was dried over magnesium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
- customThe precipitate was recrystallized with ethyl acetate
- filtrationfiltered off
Sources & evidence
- ORD record
- ord-5659fba9de034669956957442858295b
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06852744B2
Reaction notes
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