반응 #979

반응 방정식

3-indolebutyric acid

N,N-diisopropylethylamine

N,N-dimethylhydroxylamine hydrochloride

benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

→

amide

수율 94.3%

N-Methyl-N-Methoxy-4-(3-indolyl)butyramide

수율 94.3%

용매

acetonitrile

반응 조건

후처리

1. 1
   농축was then concentrated to dryness
2. 2
   workup.DISSOLUTIONThe residue was dissolved into ethyl acetate
3. 3
   세척washed with water, 0.5N HCl, saturated NaHCO3 and brine
4. 4
   건조dried over MgSO4
5. 5
   농축concentrated
6. 6
   세척Flash chromatography (elution with a gradient of 2-10% ether in methylene chloride)

실험 절차

To a slurry of 1.75 g (8.61 mmol) of 3-indolebutyric acid (Aldrich Chemical Co.) in acetonitrile at room temperature was added 7.0 mL (40.2 mmol) of N,N-diisopropylethylamine, 1.0 g (10.3 mmol) of N,N-dimethylhydroxylamine hydrochloride and 4.19 g (9.5 mmol) of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent) and the resulting mixture was allowed to stir at room temperature overnight and was then concentrated to dryness. The residue was dissolved into ethyl acetate and washed with water, 0.5N HCl, saturated NaHCO3 and brine and then dried over MgSO4 and concentrated. Flash chromatography (elution with a gradient of 2-10% ether in methylene chloride) provided 2.0 g of the amide 139. 1H NMR consistent with structure.

출처