Reaktion #45624

Reaktionsgleichung

benzyloxyacetyl chloride

tetrahydrofuran

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

sodium hydrogencarbonate

→

compound

Ausbeute 77.2%

2-(Benzyloxy)-N-(3-cyano-6-fluoro-5-hydroxy-2-methyl[1,1′-biphenyl]-4-yl)acetamide

Ausbeute 77.2%

Lösungsmittel

Ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled with ice
2. 2
   Waschenby washing with water and saturated brine
3. 3
   TrocknenThe obtained organic layer was dried over anhydrous sodium sulfate
4. 4
   Sonstigethe solvent was evaporated away under reduced pressure
5. 5
   SonstigeThe resulting residue was recrystallized
6. 6
   Sonstigepurified with n-hexane/ethyl acetate

Vorschrift

Under nitrogen atmosphere, benzyloxyacetyl chloride (489 μl, 3.10 mmol) was dropwise added to a tetrahydrofuran solution (10 ml) of 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (500 mg, 2.06 mmol) and sodium hydrogencarbonate (520 mg, 6.19 mmol) cooled with ice, followed by stirring at room temperature for 18 hours. Ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (621 mg, 1.59 mmol, 77%) as a white solid.

Quelle