Reacción #96120

Ecuación de reacción

2,2,2-trichloroethyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidine-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate

aluminum chloride

→

2,2,2-trichloroethyl 7-phenoxyacetamido-3-oxocepham-4-carboxylate

Rendimiento 124.7%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe reaction mixture is poured into ice cold diluted hydrochloric acid
2. 2
   Extracciónis extracted with ethyl acetate
3. 3
   LavadoThe extract solution is washed with diluted hydrochloric acid and water
4. 4
   Otrodried
5. 5
   Otroevaporated

Procedimiento

To a stirred solution of 2,2,2-trichloroethyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidine-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (330 mg) in methylene chloride (6 ml) is added aluminum chloride (330 mg) at room temperature, and the mixture is stirred for 60 minutes. The reaction mixture is poured into ice cold diluted hydrochloric acid, and is extracted with ethyl acetate. The extract solution is washed with diluted hydrochloric acid and water, dried, and evaporated to give 2,2,2-trichloroethyl 7-phenoxyacetamido-3-oxocepham-4-carboxylate (300 mg). Foam. IR: νmaxCHCl3 3420, 1780, 1685 cm-1. NMR: δCDCl3 3.37s2H, 4.53s2H, 4.85s2H, 5.07d(4)1H, 5.20-5.73m2H, 6.8-7.7m6H.

Fuente