Sodium hydride → HCID 57719188, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:7](=[O:19])[NH:6]1.[H-].[Na+].[CH2:23](I)[CH2:24][CH3:25]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:7](=[O:19])[N:6]1[CH2:23][CH2:24][CH3:25]Participants
Procedure
A 0° C. solution of compound [1-(4-methyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester (1.60 g, 5.8 mmol) in DMF (28 mL) is treated with sodium hydride (60% dispersion, 0.25 g, 6.4 mmol) and warmed to room temperature and stirred under N2 for 15 minutes. The resultant mixture is cooled to 0° C. and then treated with 1-propyl iodide (1.08 g, 6.4 mmol) and then warmed to room temperature and stirred for 30 minutes. The reaction is quenched with aqueous 1 N HCl (28 mL) and then worked up extractively with EtOAc and water. The organic layer is dried i and the solvent removed to give crude product that is purified by flash chromatography using a gradient of 10:1 to 1:1 hexanes:EtOAc to afford 1.40 g (76%) [1-(4-methyl-benzyl)-2,5-dioxo-3-propyl-imidazolidin-4-yl]-acetic acid methyl ester. 1H NMR. MS (ES+) Calc'd for C17H23N2O4 (M+1) 319. Found m/z 319 (100%).
Workup
- temperaturewarmed to room temperature
- stirringstirred for 30 minutes
- customThe reaction is quenched with aqueous 1 N HCl (28 mL)
- customThe organic layer is dried i
- customthe solvent removed
- customto give crude product that
- customis purified by flash chromatography
Sources & evidence
- ORD record
- ord-85cf30ed55624f3bbbcfecced258ab56
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07544812B2
Reaction notes
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