Process for the manufacture of 7.beta.-amino-3-cephem-3-ol-4 carboxylic acid compounds

Process for the manufacture of a 7.beta.-amino-3-cephem-3-ol-4-carboxylic acid compound of the formula ##STR9## wherein R.sub.1.sup.a represents an acyl group of the formula ##STR10## wherein R.sup.1 represents lower alkyl, halogeno-lower alkyl, phenyloxy-lower alkyl, hydroxyphenyloxy-lower alkyl, protected hydroxyphenyloxy-lower alkyl, halogeno-phenyloxy-lower alkyl, or lower alkyl substituted by amino and carboxyl, wherein amino is free or protected and carboxyl is free or protected, or R.sup.I represents lower alkenyl, phenyl, hydroxyphenyl, protected hydroxyphenyl, halogenophenyl, hydroxy-halogeno-phenyl, protected hydroxy-halogeno-phenyl, amino-lower alkyl-phenyl, protected amino-lower alkyl-phenyl, phenyloxyphenyl, or R.sup.I represents pyridyl, thienyl, furyl, imidazolyl or tetrazolyl, or these heterocyclic groups substituted by lower alkyl, amino, protected amino, aminomethyl or protected aminomethyl, or R.sup.I represents lower alkoxy, phenyloxy, hydroxyphenyloxy, projected hydroxyphenyloxy, halogenophenyloxy, lower alkylthio, lower alkenylthio, phenylthio, pyridylthio, 2-imidazolylthio, 1,2,4-triazol-3-ylthio, 1,3,4-triazol-2-ylthio, 1,2,4-thiadiazol-3-ylthio, 1,3,4-thiadiazol-2-ylthio, or 5-tetrazolylthio, and these heterocyclylthio groups, substituted by lower alkyl, or R.sup.I represents halogeno, lower alkoxycarbonyl, cyano, carbamoyl, N-lower alkyl-carbamoyl, N-phenylcarbamoyl, lower alkanoyl, benzoyl, or azido, or R.sub.1.sup.a represents an acyl group of the formula ##STR11## wherein R.sup.I represents lower alkyl, phenyl, hydroxyphenyl, protected hydroxyphenyl, halogenophenyl, hydroxy-halogenophenyl, protected hydroxy-halogeno-phenyl, furyl, thienyl, or isothiazolyl, or 1,4-cyclohexadienyl, and R.sup.II represents amino, protected amino, azido, carboxyl, protected carboxyl, cyano, sulpho, hydroxyl, protected hydroxyl, O-lower alkyl-phosphono, O,O'-di-lower alkyl-phosphono or halogeno, R.sub.2 represents hydroxyl, or a group R.sub.2.sup.A which is halogen or which together with the carbonyl grouping --C(=O)-- forms an esterified protected carboxyl group, and R.sub.3 represents hydrogen, lower alkyl, phenyl-lower alkyl, diphenyl-lower alkyl or tri-lower alkyl silyl, the corresponding 2-cephem compound of the formula ##STR12## wherein R.sub.1.sup.a, R.sub.2.sup.A and R.sub.3 have the abovementioned meanings, or a mixture of a compound of the formula IA and IB, or salts of such compounds with salt-forming groups, characterised in that a compound of the formula ##STR13## wherein R.sub.1.sup.a, and R.sub.2.sup.A have the meanings mentioned under formula IA, R.sub.3.sup..degree. represents lower alkyl phenyl-lower alkyl, diphenyllower alkyl or tri-lower alkyl silyl, and Y represents a leaving group of the formula --S-R.sub.4, wherein R.sub.4 is 1-methyl-imidazol-2-yl, 1,3-thiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4,5-thiatriazol-2-yl, 1,3-oxazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,3,4,5-oxatriazol-2-yl, 2-quinolyl, 1-methyl-benzimidazol-2-yl, benzthiazol-2-yl or benzoxazol-2-yl, or Y represents a leaving group of the formula --SO.sub.2 -R.sub.5, wherein R.sub.5 represents phenyl, or phenyl substituted by lower alkyl, lower alkoxy, halogen, phenyl, phenyloxy, or nitro, is treated in an inert solvent at temperatures of between room temperature and 50.degree. C. with a diazabicycloalkene, a tetra-lower alkylguanidine or a trilower alkylamine.