Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Pyridine | HCID 1049 | — |
| Edukt | 4-Methylmorpholine | HCID 7972 | — |
| Edukt | (4-Methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-((2-phenylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate | HCID 10874591 | — |
| Edukt | 2-(2-t-Butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetyl chloride | HCID 53903221 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | HCID 123160304 | HCID 123160304 | 94% |
Reaktionsschritte
To a suspension of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (1) p-toluenesulfonate (4.33 g; 8 mMol.) in dichloromethane (40 ml) is added at 0° C. N-methylmorpholine (0.88 g; 1 Eq.), pyridine (0.8 ml; 1.2 Eq.) and 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetyl chloride (1.2 Eq.). After keeping at 0° C. for 30 minutes, the reaction mixture is diluted with water and ethyl acetate and ethyl acetate layer is taken. This is washed with ##STR19## water, dried and concentrated under reduced pressure. The residue is purified by silica gel chromatography (using toluene:ethyl acetate) to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (4.89 g).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US05134138 |
|---|
| Quelldatensatz | uspto-grants-1992_07 |
|---|
| ORD ID | ord-2e70054aa9af4718b8da2635ea424b74 |
|---|
| Quellennotiz | uspto-grants-1992_07 |
|---|
