Reacción #45624

Ecuación de reacción

benzyloxyacetyl chloride

tetrahydrofuran

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

sodium hydrogencarbonate

→

compound

Rendimiento 77.2%

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

Rendimiento 77.2%

Disolventes

Ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled with ice
2. 2
   Lavadoby washing with water and saturated brine
3. 3
   SecadoThe obtained organic layer was dried over anhydrous sodium sulfate
4. 4
   Otrothe solvent was evaporated away under reduced pressure
5. 5
   OtroThe resulting residue was recrystallized
6. 6
   Otropurified with n-hexane/ethyl acetate

Procedimiento

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.

Fuente