반응 #45776

반응 방정식

citric acid

Triethylamine

cyclobutanecarbonyl chloride

2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile

→

compound

수율 85.0%

4-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclobutanecarboxylate

수율 85.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타the solvent was evaporated away under, reduced pressure
2. 2
   workup.ADDITIONEthyl acetate was added to the resulting residue
3. 3
   세척by washing with saturated brine
4. 4
   건조The organic layer was dried over anhydrous magnesium sulfate
5. 5
   기타the solvent was evaporated away under reduced pressure

실험 절차

Under nitrogen atmosphere, 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (250 mg, 1.03 mmol) was dissolved in acetonitrile (0.10 ml), and cooled to 0° C. Triethylamine (244 μl, 1.75 mmol) and cyclobutanecarbonyl chloride (177 μl, 1.55 mmol) were dropwise added to the solution, followed by stirring at room temperature for 1 hour. 10% citric acid was added to the reaction liquid, and the solvent was evaporated away under, reduced pressure. Ethyl acetate was added to the resulting residue, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with ethyl acetate/hexane (1:4, v/v) gave the entitled compound (283 mg, 85%) as a white solid.

출처