Water → HCID 57524407, compound

HRID 532116Notes

Reaction equation

HRID 532116 reaction equation
C([O:3][C:4]1[CH:5]=[C:6]([C@H:11]([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3[NH:27][C:28](=[O:31])[CH2:29][OH:30])[C:18]2=[O:32])[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:7]=[CH:8][C:9]=1[OH:10])C.[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl>[OH:3][C:4]1[CH:5]=[C:6]([C@H:11]([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3[NH:27][C:28](=[O:31])[CH2:29][OH:30])[C:18]2=[O:32])[CH2:12][S:13]([CH3:16])(=[O:14])=[O:15])[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 575244081384440-08-7

Product 1

HCID 57524407HCID 57524407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)—N-{2-[1-(3-ethoxy-4-hydroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-2-hydroxy-acetamide (0.55 mmol) in anhydrous CH2Cl2 is added AlCl3 (2.20 mmol) at room temperature. After stirring for 1 hour, water is added. The product is extracted into CH2Cl2. The solvent is removed in vacuo to give crude (S)—N-{2-[1-(3,4-dihydroxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-2-hydroxy-acetamide. The product is purified by column chromatography or recrystallization.

Workup

  1. extractionThe product is extracted into CH2Cl2
  2. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-6d4a9d676b77411989d334eb5a417783
Source dataset
uspto-grants-2014_10
Patent number
US08853175B2

Reaction notes

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