Sodium Carbonate → 7-Amino-3-(5-carboxymethyl-1,3,4-oxadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

HRID 258684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 258684
[C:1]([CH2:4][C:5]1[O:6][C:7]([SH:10])=[N:8][N:9]=1)([OH:3])=[O:2].CC(O[CH2:15][C:16]1[CH2:25][S:24][C@@H:19]2[C@H:20]([NH2:23])[C:21](=[O:22])[N:18]2[C:17]=1[C:26]([OH:28])=[O:27])=O.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O>[NH2:23][CH:20]1[C:21](=[O:22])[N:18]2[C:17]([C:26]([OH:28])=[O:27])=[C:16]([CH2:15][S:10][C:7]3[O:6][C:5]([CH2:4][C:1]([OH:3])=[O:2])=[N:9][N:8]=3)[CH2:25][S:24][C@H:19]12

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178525247HCID 178525247, Verbindung

Produkt 1

HCID 706204657-Amino-3-(5-carboxymethyl-1,3,4-oxadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 9.61 g (0.06 mol) of 2-carboxymethyl-1,3,4-oxadiazole-5-thiol in 120 ml of acetone is added to a warm (45°) solution of 10.9 g (0.04 mol) of 7-aminocephalosporanic acid in a mixture of 220 ml of water, 50 ml of acetone and 13.44 g (0.16 mol) of sodium bicarbonate. The temperature is raised to 65° and the pH maintained at 7.4-7.6 by addition of aqueous sodium carbonate solution. After 3 hours, the acetone is removed in vacuo and the reaction mixture is cooled to 10° and adjusted to pH 3.5 by addition of dilute hydrochloric acid. The product is collected, washed with water and then acetone to give the title compound.

Aufarbeitung

  1. temperatureThe temperature is raised to 65°
  2. customthe acetone is removed in vacuo
  3. temperaturethe reaction mixture is cooled to 10°
  4. additionadjusted to pH 3.5 by addition of dilute hydrochloric acid
  5. customThe product is collected
  6. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-fb06aeffb2dc439ebf5b067d333d5175
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04034092

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