Process for preparing 7 .alpha.-alkoxycephalosporin derivatives
AssigneeSankyo Company, Limited
InventorsHiroaki Yanagisawa, Akiko Ando, Masami Fukushima, Hideo Nakao
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Abstract
A process for introducing an alkoxy group into the 7.alpha.-position of a 7-amino-3-cephem-4-carboxylic acid derivative which comprises oxidizing a salt of 7-benzylideneamino-3-cephem-4-carboxylic acid derivative and reacting the product with an alkanol. The 7.alpha.-alkoxy-3-cephem-4-carboxylic acid derivatives obtained by the present invention are useful as intermediates for the synthesis of antibacterial agents.
Claims7
A process for the preparation of 7.beta.-benzylideneamino-7.alpha.-alkoxy-3-cephem compounds having the formula ##STR7## wherein R represents an alkyl group having 1-4 carbon atoms, R.sup.1 represents a hydrogen atom, methyl group, cyanomethyl group, an acyloxymethyl group, carbamoyloxymethyl group, an alkoxymethyl group, an alkylthiomethyl group or a heterocyclic thiomethyl group selected from the group consisting of 2-pyridylthiomethyl, 1-methyl-1H-tetrazol-5-ylthiomethyl, 2-(1,3,5-triazolo)thiomethyl, 2-pyrazolothiomethyl, 1-imidazolinylthiomethyl and 5-methyl-1,3,4-thiadiazolyl-2-thiomethyl, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different and each represents a hydrogen atom or a straight or branched alkyl group having 1-4 carbon atoms, n is an integer of 1 or 2 and Y.sup.+ is a cation selected from the group consisting of an alkali metal ion and an ammonium ion having the formula ##STR8## wherein R.sub.a, R.sub.b, R.sub.c and R.sub.d can be the same of different and each represents, a hydrogen atom, a straight or branched alkyl group having 1-8 carbon atoms, a cycloalkyl group having 5-7 carbon atoms, phenyl group or a phenylalkyl group having 1-4 carbon atoms in the alkyl moiety, or R.sub.a and R.sub.b can be linked together with N to form a saturated heterocyclic ring selected from the group consisting of pyrrolidine, piperidine and morpholine, or R.sub.a, R.sub.b and R.sub.c can be linked together with the N atom thereof to form a heteroaromatic ring selected from the group consisting os pyridine, picoline, lutidine, quinoline, quinaldine and pyrimidine, which comprises oxidizing a 7-benzylideneamino-3-cephem compound having the formula ##STR9## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, n and Y.sup.+ are as defined above with an oxidizing agent selected from the group consisting of lead dioxide, manganese dioxide, dicyanodichlorobenzoquinone, tert.-butylhypochlorite, N-bromosuccinimide and N-chlorosuccinimide, and contacting the resulting oxidation product with an alkanol having 1-4 carbon atoms.
Dependencies are inferred from the claim text.