Reacción #214282

Ecuación de reacción

phosphoric acid

sodium bicarbonate

3-carbamoyloxymethyl-7-(3-oxo-4-thiocyanatobutyramido)-3-cephem-4-carboxylic acid

ethyl acetate

→

3-carbamoyloxymethyl-7-(2-oxo-2,3-dihydrothiazol-4-yl)acetamido-3-cephem-4-carboxylic acid

Rendimiento 30.3%

Disolventes

phosphate

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter the reaction
2. 2
   Otrothe ethyl acetate layer was separated
3. 3
   ExtracciónThe remaining aqueous layer was further extracted with ethyl acetate
4. 4
   Lavadowashed with a saturated aqueous solution of sodium chloride
5. 5
   Secadodried over magnesium sulfate
6. 6
   workup.ADDITIONtreated with activated carbon
7. 7
   workup.DISTILLATIONthe solvent was distilled off
8. 8
   Filtracióncollected by filtration
9. 9
   Otrodried

Procedimiento

To a solution of sodium bicarbonate (0.067 g.) in pH 6.4 phosphate buffer (5 ml.) was gradually added 3-carbamoyloxymethyl-7-(3-oxo-4-thiocyanatobutyramido)-3-cephem-4-carboxylic acid (0.33 g.) with stirring at room temperature, and then the mixture was allowed to stand for 30 hours at room temperature. After the reaction, to the reaction mixture was added ethyl acetate (50 ml.). The reaction mixture was adjusted to pH 2 with 50% phosphoric acid, and then the ethyl acetate layer was separated therefrom. The remaining aqueous layer was further extracted with ethyl acetate. The ethyl acetate layers were combined together, washed with a saturated aqueous solution of sodium chloride dried over magnesium sulfate, treated with activated carbon and then the solvent was distilled off. The residue was pulverized in diethyl ether, collected by filtration and then dried to give 3-carbamoyloxymethyl-7-(2-oxo-2,3-dihydrothiazol-4-yl)acetamido-3-cephem-4-carboxylic acid (0.1 g.). The IR Spectrum and NMR Spectrum of this object compound were identical as those of the object compound obtained in Example 15.

Fuente