Water → HCID 57524406, compound

HRID 532115Notes

Reaction equation

HRID 532115 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

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 57524404Apremilast

Product 1

HCID 57524406HCID 57524406, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. extractionThe product is extracted into CH2Cl2
  2. extractionthe organic extract
  3. dry with materialis dried over MgSO4
  4. customThe solvent is removed
  5. customto afford crude (S)-4-amino-2-[1-(3,4-dihydroxy-phenyl)-2-methanesulfonyl-ethyl]-iso indole-1,3-d lone
  6. customThe product is purified by column chromatography or recrystallization

Sources & evidence

ORD record
ord-8d1b30719da54ebd8fd892163f2d63fe
Source dataset
uspto-grants-2014_10
Patent number
US08853175B2

Reaction notes

Loading…