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

HRID 706233노트

반응식

HRID 706233 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

반응 조건

온도
105 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-890adc9402ca4d09b9f263a0a6ba1812
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174976B2

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