Oxalyl chloride → Pivaloyloxymethyl 7-[(4-(3-azidopropyl)-1-piperidyl)-methyleneamino]-3-methyl-3-cephem-4-carboxylate
Reaktionsgleichung
[CH:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][N:12]=[N+:13]=[N-:14])[CH2:5][CH2:4]1)=O.C(Cl)(=O)C(Cl)=O.[NH2:21][CH:22]1[C:41](=[O:42])[N:24]2[C:25]([C:30]([O:32][CH2:33][O:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:31])=[C:26]([CH3:29])[CH2:27][S:28][C@H:23]12>C(N(CC)CC)C>[N:12]([CH2:11][CH2:10][CH2:9][CH:6]1[CH2:7][CH2:8][N:3]([CH:1]=[N:21][CH:22]2[C:41](=[O:42])[N:24]3[C:25]([C:30]([O:32][CH2:33][O:34][C:35](=[O:40])[C:36]([CH3:37])([CH3:38])[CH3:39])=[O:31])=[C:26]([CH3:29])[CH2:27][S:28][C@H:23]23)[CH2:4][CH2:5]1)=[N+:13]=[N-:14]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -10 °C
Versuchsvorschrift
A solution of N-formyl-4-(3-azidopropyl)-piperidine (1.13 g) in alcohol-free chloroform (2.5 ml) was cooled to -20° C. and oxalyl chloride (0.44 ml) in alcohol-free chloroform (2.5 ml) was added dropwise. After 1 hour at -20° C. the solution was added dropwise at -60° C. to -70° C. to a stirred solution of pivaloyloxymethyl 7-amino-3-methyl-3-cephem-4-carboxylate (1.72 g) in alcohol-free chloroform (12 ml). Triethylamine (1.46 ml) was added and within the next hour the temperature was gradually raised to -10° C. The solvent was evaporated and the residue was extracted with ether. The ether extract was evaporated to leave an oil, which was purified by column chromatography on Sephadex to yield the desired compound as a yellow oil.
Aufarbeitung
- customThe solvent was evaporated
- extractionthe residue was extracted with ether
- extractionThe ether extract
- customwas evaporated
- customto leave an oil, which
- customwas purified by column chromatography on Sephadex
Quellen und Nachweise
- ORD-Eintrag
- ord-373c942d19a845488de9d8032787a560
- Quelldatensatz
- uspto-grants-1981_03
- Patentnummer
- US04259333
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