Water → HCID 78023603, compound

HRID 1844568Notes

Reaction equation

COP([CH2:7][C:8]([O:10][CH3:11])=[O:9])(OC)=O.[H-].[Na+].[C:14]1(=[O:28])[N:18]([CH2:19][C:20](=O)[CH3:21])[C:17](=[O:23])[C:16]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:15]12.O>CN(C)C=O>[O:23]=[C:17]1[C:16]2[C:15](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14](=[O:28])[N:18]1[CH2:19][C:20]([CH3:21])=[CH:7][C:8]([O:10][CH3:11])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methyl dimethylphosphonoacetate (21.5 g) in N,N-dimethylformamide (50 mL) was added dropwise to a suspension of sodium hydride (63%, 4.50 g) in N,N-dimethylformamide (100 mL) with stirring at 0° C. The mixture was stirred at 0° C. for 30 minutes. Then, a solution of phthalimidoacetone (20.0 g) in N,N-dimethylformamide (50 mL) was added dropwise thereto, and the mixture was heated to room temperature and stirred overnight. To the reaction solution, water was added, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride and saturated sodium chloride solution and dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the obtained crude product was purified by silica gel column chromatography to obtain the title compound (20.6 g).

Workup

stirringThe mixture was stirred at 0° C. for 30 minutes
temperaturethe mixture was heated to room temperature
stirringstirred overnight
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with a saturated aqueous solution of ammonium chloride and saturated sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
filtrationAfter filtration and concentration under reduced pressure
customthe obtained crude product
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-b7304fb5b1aa4653bbcd17e6d248dd4e
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946443B2

Reaction notes

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