تفاعل #4866

معادلة التفاعل

(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

المردود 59.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   ترشيحInsoluble materials are filtered off
2. 2
   تركيزthe filtrate is concentrated to dryness under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue is dissolved in ethyl acetate
4. 4
   غسيلwashed with 1% hydrochloric acid, 5% aqueous sodium bicarbonate solution
5. 5
   تجفيفThe ethyl acetate solution is then dried
6. 6
   تركيزconcentrated to dryness under reduced pressure
7. 7
   أخرىThe residue thus obtained
8. 8
   أخرىis purified by silica gel chromatography (solvent, ethyl acetate:benzene=5:2)

الإجراء التجريبي

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.

المصدر