Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:35].[OH-].[Li+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:35]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Chloro-7-[1-(tert-butoxycarbonyl)-5-(ethoxycarbonylmethylaminomethyl)indol-2-yl]isoindolinone (43.4 mg) was dissolved in DMF (2 mL), and the solution was added with 4 mol/L aqueous lithium hydroxide solution (1 mL), followed by stirring at room temperature for 1 hour. The reaction mixture was added with 1 mol/L hydrochloric acid, extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-5-(carboxymethylaminomethyl)indol-2-yl]isoindolinone (25.0 mg).
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-778c1b77740246e6a4b8de52e93d39dd
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745641B2
Linked notes
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