Ethyl Acetate → [5-(2-Dimethylamino-benzooxazol-5-yloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester

HRID 706233ノート

反応式

HRID 706233 の反応式
[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

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 671102512-(Dimethylamino)benzo[d]oxazol-5-ol

生成物 1

HCID 67110267[5-(2-Dimethylamino-benzooxazol-5-yloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester

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

  1. temperaturewas cooled to room temperature
  2. custompartitioned between chloroform and water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. 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-890adc9402ca4d09b9f263a0a6ba1812
出典データセット
uspto-grants-2015_11
特許番号
US09174976B2

反応ノート

読み込み中…