p-Toluenesulfonic acid → 7-Amino-3vinyl-3-cephem-4-carboxylic acid

HRID 569350

Reaktionsgleichung

Cl.[NH2:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:13])=[C:7]([CH:10]=[CH2:11])[CH2:8][S:9][C@H:4]12.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>CO.C1(OC)C=CC=CC=1>[NH2:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([OH:14])=[O:13])=[C:7]([CH:10]=[CH2:11])[CH2:8][S:9][C@H:4]12

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a suspension of benzhydryl 7-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride (48 g) in methanol (250 ml) and anisole (70 ml) was added p-toluenesulfonic acid (85 g), and the mixture was stirred at 50° C. for 2 hours. The reaction mixture was poured into 10% aqueous sodium carbonate (600 ml) and ethyl acetate (700 ml), followed by adjusting to pH 7.5 with 20% aqueous sodium carbonate. The separated aqueous solution was washed with ethyl acetate (500 ml) and then adjusted to pH 2.5 with conc. hydrochloric acid, followed by stirring under ice-cooling for an hour. The precipitated crystals were collected by filtration and washed with acetone to obtain 7-amino-3-vinyl-3-cephem-4-carboxylic acid (15.4 g), mp 200° to 230° C. (dec.).

Aufarbeitung

washThe separated aqueous solution was washed with ethyl acetate (500 ml)
stirringby stirring under ice-
temperaturecooling for an hour
filtrationThe precipitated crystals were collected by filtration
washwashed with acetone

Quellen und Nachweise

ORD-Eintrag: ord-e9b803ed96ae48b691fc861dea4e89f6
Quelldatensatz: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04731443

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