Chloride → [3-(4-Methoxy-benzyl)-1-naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[C:7](=[O:22])[NH:6]1.[H-].[Na+].[Cl-].CN([CH:30]=[O:31])C>>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[C:7](=[O:22])[N:6]1[CH2:11][C:12]1[CH:21]=[CH:20][C:19]([O:31][CH3:30])=[CH:14][CH:13]=1Komponenten
Versuchsvorschrift
A 0° C. solution of compound (1-naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl)-acetic acid methyl ester (6.29 g, 20.1 mmol) in DMF (60 mL) is treated with sodium hydride (60% dispersion, 0.97 g, 24.3 mmol) and warmed to room temperature and stirred under N2 for 20 minutes. The resultant mixture is cooled to 0° C. and then treated with 4-methoxybenzyl, chloride (6.35 g, 40.6 mmol) and then warmed to room temperature and stirred for 16 hours. The reaction is quenched with aqueous 1 N HCl (100 mL) and then worked up extractively with Et2O and water. The organic layer is dried and the solvent removed to give crude product that is purified by flash chromatography using a gradient of 4:1 hexanes:acetone to afford 8.31 g (95%) [3-(4-methoxy-benzyl)-1-naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester. Rf=0.44 (1:1 hexanes:acetone). 1H NMR.
Aufarbeitung
- temperaturewarmed to room temperature
- stirringstirred for 16 hours
- customThe reaction is quenched with aqueous 1 N HCl (100 mL)
- customThe organic layer is dried
- customthe solvent removed
- customto give crude product that
- customis purified by flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-b340af43658d4e4086c4ab1adb7fbd76
- Quelldatensatz
- uspto-grants-2009_06
- Patentnummer
- US07544812B2
Notizen zur Reaktion
Wird geladen…