Succinimide → 3-(3-pyrrolidine-2,5-dione-1-ylmethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

HRID 562552Notes

Reaction equation

HRID 562552 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.CC([O-])(C)C.[K+].Br[CH2:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:26]=[C:25]([CH2:27][CH:28]([CH3:30])[CH3:29])[S:24][C:23]=2[S:31]([NH:34][C:35]([CH3:38])([CH3:37])[CH3:36])(=[O:33])=[O:32])[CH:19]=[CH:20][CH:21]=1>CS(C)=O.C(Cl)Cl>[N:5]1([CH2:15][C:16]2[CH:17]=[C:18]([C:22]3[CH:26]=[C:25]([CH2:27][CH:28]([CH3:30])[CH3:29])[S:24][C:23]=3[S:31]([NH:34][C:35]([CH3:37])([CH3:36])[CH3:38])(=[O:32])=[O:33])[CH:19]=[CH:20][CH:21]=2)[C:4](=[O:6])[CH2:3][CH2:2][C:1]1=[O:7]

Participants

6

Reactant 3

HCID 11439SuccinimideHCID 23665647Potassium tert-butoxideHCID 670039813-(3-Bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

Product 1

HCID 670045673-(3-pyrrolidine-2,5-dione-1-ylmethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamideYield 94%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of succinimide (66.6 mg, 0.672 mmol) in DMSO (1 mL) and t-BuOK (52.8 mg, 0.470 mmol), that had been stirred for 40 min at ambient temperature, was added a solution of 3-(3-bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide (99.5 mg, 0.224 mmol; see step (e)) in DMSO (1 mL) dropwise. The reaction mixture was stirred for 1 h at ambient temperature and then diluted with CH2Cl2 (15 mL). The organic layer was washed with water, dried (over anhydrous MgSO4), concentrated in vacuo, and the residue purified by flash chromatography using MeOH:CH2Cl2 (3:97) as eluent to give the sub-title compound in 94% yield as a colourless syrup (97.1 mg, 0.210 mmol).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried (over anhydrous MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-0ff4c016adfb4f1e815a713d885a3ec2
Source dataset
uspto-grants-2011_11
Patent number
US08067418B2

Reaction notes

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