Sodium Bicarbonate → Cefazolin deacylated

HRID 2285641

Reaktionsgleichung

Reaktionsgleichung von HRID 2285641
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9]OC(=O)CC(=O)C)[CH2:7][S:8][C@H:3]12.C(=O)([O-])O.[Na+].[SH:27][C:28]1[S:29][C:30]([CH3:33])=[N:31][N:32]=1>O>[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:27][C:28]3[S:29][C:30]([CH3:33])=[N:31][N:32]=3)[CH2:7][S:8][C@H:3]12

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acidHCID 178434161HCID 178434161, Verbindung

Produkt 1

HCID 6350581Cefazolin deacylatedAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In water (30 ml) was dissolved 7β-amino-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid (3.14 g) together- with sodium hydrogen carbonate (1.84 g) and 2-mercapto-5-methyl-1,3,4-thiadiazole (1.6 g) and the resultant solution was adjusted its pH to 6.4, followed by stirring for one hour at 60° C. After cooling, the reaction solution was washed with dichloromethane and pH of the aqueous layer was adjusted to 3.5 under ice-cooling, followed by stirring for one hour. The precipitated materials were collected by filtration and washed with water, methanol and acetone in this order, followed by drying to give 7β-amino-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (2.9 g).

Aufarbeitung

  1. temperatureAfter cooling
  2. washthe reaction solution was washed with dichloromethane and pH of the aqueous layer
  3. temperaturecooling
  4. stirringby stirring for one hour
  5. filtrationThe precipitated materials were collected by filtration
  6. washwashed with water, methanol and acetone in this order
  7. customby drying

Quellen und Nachweise

ORD-Eintrag
ord-08d6f530993d4d77a871e1ec49768601
Quelldatensatz
uspto-grants-1982_04
Patentnummer
US04323676

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