Reacción #57294

Ecuación de reacción

10

4-(4-cyclopropylethynyl-2-oxo-4-trifluoromethyl-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yloxy)-butyric Acid Ethyl Ester

lithium hydroxide

→

11

Rendimiento 83.0%

4-(4-cyclopropylethynyl-2-oxo-4-trifluoromethyl-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yloxy)-butyric Acid

Rendimiento 83.0%

Disolventes

methanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated under reduced pressure
2. 2
   workup.ADDITIONTo the residue 20 mL of water were added
3. 3
   ExtracciónThe reaction mixture was extracted with 4×30 mL of ethyl acetate
4. 4
   Secadodried (Na2SO4)
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe residue was purified by preparative thin layer chromatography (silica gel, 2 mm thickness, E. Merck)

Procedimiento

To a suspension of 45 mg (0.11 mmol) of 10 in 4 mL of 50% methanol in water was added 60 mg (2.5 mmol) of lithium hydroxide. The reaction mixture was allowed to stir at room temperature for 1 hour and concentrated under reduced pressure. To the residue 20 mL of water were added followed by 1 mL of 1N HCl. The reaction mixture was extracted with 4×30 mL of ethyl acetate. The organic layers were combined, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography (silica gel, 2 mm thickness, E. Merck) using 5% methanol in dichloromethane to give 35 mg (0.091 mmol, 83%) of 11.

Fuente