Reacción #56083

Ecuación de reacción

benzyl 7β-(α-phenyl-α-carbobenzoxyaminoacetamido)-3-chloro-3-cephem-4-carboxylate

aluminum chloride

→

7β-(α-phenyl-glycinamido)-3-chloro-3-cephem-4-carboxylic acid

Rendimiento 91.4%

Disolventes

methylene chloride

nitromethane

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with dilute hydrochloric acid
2. 2
   Extracciónextracted with an aqueous solution of 5% sodium hydrogen carbonate
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe extract is washed with water
5. 5
   Otrodried
6. 6
   Otroevaporated
7. 7
   OtroThe residue is recrystallized from a mixture of ethyl acetate and ether

Procedimiento

To a solution of benzyl 7β-(α-phenyl-α-carbobenzoxyaminoacetamido)-3-chloro-3-cephem-4-carboxylate (295 mg) in methylene chloride (6 ml) is added a solution of aluminum chloride (267 mg) in nitromethane (3 ml) under ice cooling. After stirring for 2 hours at room temperature, the mixture is diluted with ethyl acetate, washed with dilute hydrochloric acid, and extracted with an aqueous solution of 5% sodium hydrogen carbonate. The extract is acidified with hydrochloric acid and extracted with ethyl acetate. The extract is washed with water, dried, and evaporated. The residue is recrystallized from a mixture of ethyl acetate and ether to give 7β-(α-phenyl-glycinamido)-3-chloro-3-cephem-4-carboxylic acid (167 mg). Yield: 91.4%.

Fuente