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

HRID 562554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 562554
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1c3bf569944944388d5fbd0f71aa13b3
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067418B2

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