Chloride → [3-(4-Methoxy-benzyl)-1-naphthalen-2-ylmethyl-2,5-dioxo-imidazolidin-4-yl]-acetic acid methyl ester
反応式
[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]=1参加物
実験手順
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.
後処理
- 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
出典と根拠
- ORDレコード
- ord-b340af43658d4e4086c4ab1adb7fbd76
- 出典データセット
- uspto-grants-2009_06
- 特許番号
- US07544812B2
反応ノート
読み込み中…