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

HRID 562552ノート

反応式

HRID 562552 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0ff4c016adfb4f1e815a713d885a3ec2
出典データセット
uspto-grants-2011_11
特許番号
US08067418B2

反応ノート

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