反応 #4866

反応方程式

(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

収率 59.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   ろ過Insoluble materials are filtered off
2. 2
   濃縮the filtrate is concentrated to dryness under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue is dissolved in ethyl acetate
4. 4
   洗浄washed with 1% hydrochloric acid, 5% aqueous sodium bicarbonate solution
5. 5
   乾燥The ethyl acetate solution is then dried
6. 6
   濃縮concentrated to dryness under reduced pressure
7. 7
   その他The residue thus obtained
8. 8
   その他is purified by silica gel chromatography (solvent, ethyl acetate:benzene=5:2)

実験手順

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.

出典