Reaktion #45839

Reaktionsgleichung

citric acid

Triethylamine

cyclopentanecarbonyl chloride

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

→

compound

Ausbeute 72.0%

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

Ausbeute 72.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent was evaporated away under reduced pressure
2. 2
   workup.ADDITIONEthyl acetate was added to the resulting residue
3. 3
   Waschenby washing with saturated brine
4. 4
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Sonstigethe solvent was evaporated away under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by preparative TLC (ethyl acetate

Vorschrift

Under nitrogen atmosphere, 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (200 mg, 0.83 mmol) was dissolved in acetonitrile (10 ml), and cooled at 0° C. Triethylamine (138 μl, 1.36 mmol) and cyclopentanecarbonyl chloride (138 μl, 1.36 mmol) were dropwise added to the solution, followed by stirring at room temperature for 2 hours. 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 purified by preparative TLC (ethyl acetate:n-hexane=1:3, v/v) to obtain the entitled compound (200 mg, 72%) as a colorless oil.

Quelle