반응 #730229

반응 방정식

2-Fluoro ethylamine

triethylamine

3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid

EDCI

→

3-(5-dimethylcarbamoyl-pent-1-ynyl)-N-(2-fluoro-ethyl)benzamide

수율 91.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture stirred at room temperature for 16 hrs
2. 2
   세척The reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL)
3. 3
   기타The organic layer was separated
4. 4
   건조dried over magnesium sulfate
5. 5
   기타the solvent evaporated under vacuum
6. 6
   기타The residue was purified by flash column chromatography on silica gel (DCM:MeOH, 95% to 5% methanol gradient)

실험 절차

To a solution of 3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid (0.100 g, 0.38 mmol) in dry dichloromethane (1.5 mL) under a nitrogen atmosphere at room temperature, EDCI (0.0728 g, 0.38 mmol) was added followed by triethylamine (0.162 mL, 1.14 mmol), the resulting mixture was stirred at room temperature for further 5 minutes. 2-Fluoro ethylamine (0.189 g, 1.9 mmol) was then added and the mixture stirred at room temperature for 16 hrs. The reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL) followed by saturated brine solution (100 mL). The organic layer was separated and dried over magnesium sulfate and the solvent evaporated under vacuum. The residue was purified by flash column chromatography on silica gel (DCM:MeOH, 95% to 5% methanol gradient) to afford 3-(5-dimethylcarbamoyl-pent-1-ynyl)-N-(2-fluoro-ethyl)benzamide (26)(0.103 g, 0.34 mmol, 91% yield).

출처