Diisopropyl Ether → HCID 13920705, compound

Participants

Reaction Steps

To a mixture of 7-aminocephalosporanic acid (45.0 g) and potassium thiocyanate (14.55 g) in acetonitrile (225 ml) was added dropwise trifluoromethanesulfonic acid (67.5 g) below 18° C. under cooling in an ice-bath and stirring, which was continued for 30 minutes at 15° to 18° C. The reaction mixture containing 7-amino-3-cyanothiomethyl-3-cephem-4-carboxylic acid was added to a mixture of pyridine (118.5 g) and water (150 ml) at 30° to 33.5° C. under stirring. The resultant mixture was immediately poured into a cold mixture of isopropyl alcohol (900 ml) and diisopropyl ether (1.2 l) under cooling in an ice-bath and stirring. The resulting precipitate was filtered, washed with isopropyl alcohol and diisopropyl ether and then redissolved in water (1.0 l). An insoluble material was filtered off and the filtrate was passed through a column packed with acidic alumina (150 g). The eluate (1.38 l) was concentrated to about 60 g of weight under reduced pressure and stirred for 30 minutes under cooling in an ice-bath. The resulting precipitate was filtered, washed with methanol and diisopropyl ether and dried to give 7-amino-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate thiocyanate (12.56 g), mp. 175° to 180° C. (dec.).

Provenance & Evidence