Dichloromethane → Cephaloglycin

HRID 1834074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1834074
[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:25][S:24][C@@H:9]2[C@H:10]([NH:13][C:14]([C@H:16]([NH2:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:26]([OH:28])=[O:27])=[O:3].O.S([O-])([O-])(=O)=O.[Mg+2].C(Cl)Cl>C(N(CC)CC)C>[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:25][S:24][C@@H:9]2[C@H:10]([NH:13][C:14]([C@H:16]([NH2:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:26]([OH:28])=[O:27])=[O:3]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 7061048122202-75-1

Produkt 1

HCID 19150Cephaloglycin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a suspension consisting of 4.23 g. of cephaloglycin monohydrate, 3.0 g. of anhydrous magnesium sulfate, and 70 ml. of methylene chloride are added 3.1 ml. of triethylamine and after stirring the mixture for one hour at room temperature, magnesium sulfate was filtered off to provide a triethylamine salt solution of cephaloglycin. To the solution was added dropwise a solution of nicotinoyl chloride N-oxide prepared by adding dropwise 0.73 ml. of thionyl chloride to a solution consisting of 1.39 g. of nicotinic acid N-oxide, 1.4 ml. of triethylamine, and 30 ml. of methylene chloride under ice-cooling followed by stirring for 1.5 hours. In this case, the pH of the reaction mixture was maintained at 8-9 by adding triethylamine.

Aufarbeitung

  1. filtrationmagnesium sulfate was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-53f06f6a2a0f4de68eb9ffbfcae2a0bb
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04068074

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