434. 7-Aminocephalosporanic Acid
Nomenclature
CAS number: 957-68-6
(6R,7R)-3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic
acid; 7-amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic
acid acetate ester; 3-acetoxymethyl-7-aminoceph-3-em-4-oic acid; 7-ACA. C10H12N2O5S; mol wt 272.28.
C 44.11%, H 4.44%, N 10.29%, O 29.38%, S 11.78%.
Description and references
Starting material for semi-synthetic cephalosporins. Obtained by mild acid hydrolysis of cephalosporin C, q.v.: Loder et al., Biochem. J. 79, 408 (1961); Morin et al., J. Am. Chem. Soc. 84, 3400 (1962); Morin et al., BE 615955 (1962 to Lilly), C.A. 58, 11373c (1963); by enzymatic hydrolysis of cephalosporin C: Walton, US 3239394 (1966 to Merck & Co.). Improved prepn: Fechtig et al., Helv. Chim. Acta 51, 1108 (1968). Review of preparative methods: Huber et al., in Cephalosporins and Penicillins, E. H. Flynn, Ed. (Academic Press, New York, 1972) pp 27-73.
