Ethyl Acetate → 1H-Pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid, 5-hydroxy-, 1-(1,1-dimethylethyl) 2-ethyl ester
Reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:9]2=[N:10][CH:11]=[C:12]([O:14]C(=O)C3C=CC=CC=3)[CH:13]=[C:8]2[CH:7]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:23]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C:9]2=[N:10][CH:11]=[C:12]([OH:14])[CH:13]=[C:8]2[CH:7]=1)=[O:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2.20 g (5.36 mmol) 5-benzoyloxy pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 20 mL methanol was added 0.81 g (5.90 mmol) potassium carbonate. After 1 h the reaction was poured into ethyl acetate and extracted with 10% aqueous citric acid solution. The phases were separated and the organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:1) to give the product as a colourless oil (100%).
Workup
- extractionextracted with 10% aqueous citric acid solution
- customThe phases were separated
- washthe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:1)
Sources & evidence
- ORD record
- ord-4da3d666d57745f0bf9a0345cdaa2c9f
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07208494B2
Reaction notes
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