2-Pyrrolidone → 3-(3-pyrrolidine-2-one-1-ylmethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

HRID 562554ノート

反応式

HRID 562554 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].CC([O-])(C)C.[K+].Br[CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:25]=[C:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[S:23][C:22]=2[S:30]([NH:33][C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:32])=[O:31])[CH:18]=[CH:19][CH:20]=1>CS(C)=O.C(Cl)Cl>[N:1]1([CH2:14][C:15]2[CH:16]=[C:17]([C:21]3[CH:25]=[C:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[S:23][C:22]=3[S:30]([NH:33][C:34]([CH3:36])([CH3:35])[CH3:37])(=[O:31])=[O:32])[CH:18]=[CH:19][CH:20]=2)[CH2:5][CH2:4][CH2:3][C:2]1=[O:6]

参加物

6

反応物 3

HCID 120252-PyrrolidoneHCID 23665647Potassium tert-butoxideHCID 670039813-(3-Bromomethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

生成物 1

HCID 670049583-(3-pyrrolidine-2-one-1-ylmethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide収率 77%

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 2-pyrrolidinone (26.5 mg, 0.312 mmol) in DMSO (1 mL) and t-BuOK (48.9 mg, 0.436 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 (92.3 mg, 0.208 mmol; see Example 1(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 (2:98) as eluent to give the sub-title compound in 77% yield as a colourless syrup (72.3 mg, 0.161 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-1c3bf569944944388d5fbd0f71aa13b3
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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