Ethyl Acetate → [5-(2-Dimethylamino-benzooxazol-5-yloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester
反応式
[CH3:1][N:2]([CH3:13])[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:6]=2[N:7]=1.[CH2:14]([O:16][C:17](=[O:19])[CH3:18])[CH3:15].[C:20](=[O:23])([O-])[O-].[K+].[K+].[CH3:26][C:27]([N:29](C)C)=[O:28]>>[CH2:14]([O:16][C:17](=[O:19])[CH2:18][N:29]1[C:27](=[O:28])[C:26]2[C:8](=[CH:6][CH:5]=[C:11]([O:12][C:9]3[CH:10]=[CH:11][C:5]4[O:4][C:3]([N:2]([CH3:13])[CH3:1])=[N:7][C:6]=4[CH:8]=3)[CH:10]=2)[C:20]1=[O:23])[CH3:15]参加物
5
反応条件
- 温度
- 105 °C
実験手順
A mixture of 2-dimethylamino-benzooxazol-5-ol (4.82 g, 0.03 mmol), 5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester (8.66 g, 0.03 mmol), potassium carbonate (4.49 g, 0.03 mmol) and dimethylacetamide (30 mL) was stirred at 105° C. for twenty-two hours before it was cooled to room temperature and partitioned between chloroform and water. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a orange solid (4.24 g): MS: (+) m/z 410.2 (M+1).
後処理
- temperaturewas cooled to room temperature
- custompartitioned between chloroform and water
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- custompurified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane
出典と根拠
- ORDレコード
- ord-6ccfbf93f10c4766bbf73c3c634a49a6
- 出典データセット
- uspto-grants-2011_04
- 特許番号
- US07928120B2
反応ノート
読み込み中…