Pyridine → Benzhydryl 7-salicylideneamino-3-chloromethyl-3-cephem-4-carboxylate

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Reaktionsgleichung

[CH:1](=[N:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:14]([CH2:17]O)[CH2:15][S:16][C@H:11]12)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].P(Cl)(Cl)(Cl)(Cl)[Cl:38].N1C=CC=CC=1>C(Cl)Cl>[CH:1](=[N:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:14]([CH2:17][Cl:38])[CH2:15][S:16][C@H:11]12)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Komponenten

Reaktionsbedingungen

Temperatur: -30 °C

Versuchsvorschrift

Benzhydryl 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate (1.01 g) was dissolved in methylene chloride (10 ml) and cooled to -30° C. To this solution was added phosphorus pentachloride (0.46 g), followed by addition of pyridine (0.18 ml). The reaction mixture was stirred for an hour at -30° to -20° C. and poured into ice-water. The separated organic layer was washed with water and an aqueous sodium chloride, followed by drying over magnesium sulfate. The solvent was evaporated in vacuo to give benzhydryl 7-salicylideneamino-3-chloromethyl-3-cephem-4-carboxylate (0.9 g).

Aufarbeitung

washThe separated organic layer was washed with water
dry with materialby drying over magnesium sulfate
customThe solvent was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-9b1c3cb1330b40df9126731eed692991
Quelldatensatz: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04731443

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