Ethyl Acetate → [5-(2-Dimethylamino-benzooxazol-5-yloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester
Reaction equation
[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]Participants
5
Conditions
- Temperature
- 105 °C
Procedure
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).
Workup
- 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
Sources & evidence
- ORD record
- ord-890adc9402ca4d09b9f263a0a6ba1812
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174976B2
Reaction notes
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