Reacción #1929080

Ecuación de reacción

potassium tert-butoxide

compound

Methyl 1-{[(4′-chloro-4-methylbiphenyl-3-yl)acetyl]amino}-4,4-difluorocyclohexanecarboxylate

hydrogen chloride

→

3-(4′-Chloro-4-methylbiphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one

Disolventes

N,N-dimethylacetamide

N,N-dimethylacetamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise until a pH of 2
2. 2
   Filtraciónthe precipitate was filtered off with suction
3. 3
   Lavadowashed with water
4. 4
   OtroFor further purification
5. 5
   Extracciónextracted with 50 ml of 1N aqueous sodium hydroxide solution
6. 6
   Filtraciónfiltered off with suction
7. 7
   Lavadowashed with water and, for purification
8. 8
   Otrosuspended in 25 ml of hot acetonitrile on an ultrasonic bath
9. 9
   Filtraciónfiltered off with suction
10. 10
    Lavadowashed
11. 11
    Otrodried

Procedimiento

Under argon and at 20 to 30° C., 3.31 g (28.0 mmol) of potassium tert-butoxide in 10 ml of N,N-dimethylacetamide were added to 11.1 g (25.5 mmol) of the compound from Example 6A in 22 ml of N,N-dimethylacetamide. The reaction mixture was stirred at 30° C. for 3 h. The reaction mixture was then added to 250 ml of ice-water, 1N aqueous hydrogen chloride solution was added dropwise until a pH of 2 had been reached and the precipitate was filtered off with suction and washed with water. For further purification, the product was taken up in methylene chloride and extracted with 50 ml of 1N aqueous sodium hydroxide solution, the aqueous phase was acidified with aqueous 1 N hydrochloric acid, filtered off with suction, washed with water and, for purification, suspended in 25 ml of hot acetonitrile on an ultrasonic bath, filtered off with suction, washed and dried. This gave 5.70 g (55% of theory) of the title compound.

Fuente