Reacción #62544

Ecuación de reacción

4-Bromomethyl-5-methyl-1,3-dioxolene-2-one

sodium 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-(3-methyl-1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate

ethyl acetate

water

→

title compound

Rendimiento 62.3%

(5-Methyl-2-oxo-1,3-dioxolen-4-yl)methyl 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-(3-methyl-1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate

Rendimiento 62.3%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwith stirring
2. 2
   OtroThe ethyl acetate layer was separated
3. 3
   Lavadowashed successively with water (30 ml, adjusted to pH 3 with dil. HCl), 10% aqueous K2HPO4 solution (30 ml) twice
4. 4
   Secadosaturated saline water, dried over MgSO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   workup.ADDITIONthe residue was added dropwise to a mixture of diethyl ether (40 ml) and petroleum ether (40 ml)
7. 7
   FiltraciónThe formed crystals were filtered
8. 8
   Lavadowashed with petroleum ether
9. 9
   Otrodried in vacuo

Procedimiento

4-Bromomethyl-5-methyl-1,3-dioxolene-2-one (386 mg) was added to a solution of sodium 7-[(Z)-2-methoxyimino-2-(thiazol-4-yl)acetamido]-3-(3-methyl-1,2,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylate (536 mg) in dimethylformamide (5 ml) at -5° C. The mixture was stirred at this temperature for 1.3 hr and then poured into a mixture of ethyl acetate (130 ml) and water (30 ml, adjusted to pH 3 with dil HCl) with stirring. The ethyl acetate layer was separated, washed successively with water (30 ml, adjusted to pH 3 with dil. HCl), 10% aqueous K2HPO4 solution (30 ml) twice, and saturated saline water, dried over MgSO4, concentrated in vacuo, and the residue was added dropwise to a mixture of diethyl ether (40 ml) and petroleum ether (40 ml). The formed crystals were filtered, washed with petroleum ether, and dried in vacuo to give the title compound (390 mg). ##STR38##

Fuente