Reacción #4866

Ecuación de reacción

(Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid

benzhydryl 7β-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylate

1-hydroxybenzotriazole

dicyclohexylcarbodiimide

→

benzhydryl 7β-{(Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetamido}-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]- 3-cephem-4-carboxylate

Rendimiento 59.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónInsoluble materials are filtered off
2. 2
   Concentraciónthe filtrate is concentrated to dryness under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue is dissolved in ethyl acetate
4. 4
   Lavadowashed with 1% hydrochloric acid, 5% aqueous sodium bicarbonate solution
5. 5
   SecadoThe ethyl acetate solution is then dried
6. 6
   Concentraciónconcentrated to dryness under reduced pressure
7. 7
   OtroThe residue thus obtained
8. 8
   Otrois purified by silica gel chromatography (solvent, ethyl acetate:benzene=5:2)

Procedimiento

3.25 g of (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid are dissolved in 200 ml of tetrahydrofuran, and 3.14 g of benzhydryl 7β-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylate, 1.03 g of 1-hydroxybenzotriazole and 1.57 g of dicyclohexylcarbodiimide are added thereto. The mixture is stirred at room temperature for 2 hours. Insoluble materials are filtered off, and the filtrate is concentrated to dryness under reduced pressure. The residue is dissolved in ethyl acetate, and washed with 1% hydrochloric acid, 5% aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, successively. The ethyl acetate solution is then dried and concentrated to dryness under reduced pressure. The residue thus obtained is purified by silica gel chromatography (solvent, ethyl acetate:benzene=5:2). 3.7 g of benzhydryl 7β-{(Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetamido}-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]- 3-cephem-4-carboxylate are obtained.

Fuente