Acetone → 7-Amino-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1605215

Reaktionsgleichung

Reaktionsgleichung von HRID 1605215
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[OH-].[Na+].C[N:22]1[N:26]=[C:25]([SH:27])[S:24][CH2:23]1.Cl.[CH3:29]C(C)=O>O>[CH3:29][C:23]1[S:24][C:25]([S:27][CH2:5][C:6]2[CH2:15][S:14][CH:9]3[N:8]([C:11](=[O:12])[CH:10]3[NH2:13])[C:7]=2[C:16]([OH:18])=[O:17])=[N:26][N:22]=1

Komponenten

7

Edukt 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4413287-Aminocephalosporanic acidHCID 178481658HCID 178481658, Verbindung

Produkt 1

HCID 31498227-Amino-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 13.6 g. (0.05 M) of 7-aminocephalosporanic acid in 100 ml. of water and 50 ml. of acetone are brought to pH 8 with sodium hydroxide while stirring. 9.8 g. (0.57 M) of 3-methyl-1,3,4-thiadiazole-5-thiol are added and the mixture is heated at 80° for 4 hours. After cooling to 5°, this is acidified to pH 3.5 with dilute hydrochloric acid and stirred for 15 minutes. The precipitated solid is filtered under suction and washed with acetone. This 3[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is purified by dissolving in sodium bicarbonate solution and reprecipitating with 2N hydrochloric acid; yield 12.7 g., m.p. 206°.

Aufarbeitung

  1. additionA mixture of 13.6 g
  2. temperaturethe mixture is heated at 80° for 4 hours
  3. temperatureAfter cooling to 5°
  4. stirringstirred for 15 minutes
  5. filtrationThe precipitated solid is filtered under suction
  6. washwashed with acetone
  7. customThis 3[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is purified
  8. dissolutionby dissolving in sodium bicarbonate solution
  9. customreprecipitating with 2N hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-6421471b37d54c8cb41e67f98925b6da
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03950330

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