Water → HCID 57524406, compound

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:28])[N:5]([C@@H:12]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25]CC)[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]2=[O:11].[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:28])[N:5]([C@@H:12]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([OH:25])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]2=[O:11]

Participants

Procedure

To a stirred solution of (S)-4-amino-2-[1-(3-ethoxy-4-hydroxy-phenyl)-2-methanesulfonyl-ethyl]-isoindole-1,3-dione (0.55 mmol) in anhydrous CH2Cl2 at room temperature, is added AlCl3 (2.2 mmol). After stirring for 1 hour, water is added. The product is extracted into CH2Cl2, and the organic extract is dried over MgSO4. The solvent is removed to afford crude (S)-4-amino-2-[1-(3,4-dihydroxy-phenyl)-2-methanesulfonyl-ethyl]-iso indole-1,3-d lone. The product is purified by column chromatography or recrystallization.