Epimerization of malonic acid esters
AssigneeShionogi & Co., Ltd.
InventorsMasayuki Narisada, Hiroshi Onoue, Mitsuaki Ohtani, Fumihiko Watanabe
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Abstract
A compound represented by the formula (II) epimerizes by the action of a base and the product is precipitated for shifting the equilibrium to yield the corresponding epimer represented by the formula (I). ##STR1## wherein Ar is an optionally substituted aryl or heterocyclic group; Tet is an optionally substituted tetrazolyl group and B.sup.1 and B.sup.2 are each ester forming group in the field of penicillin or cephalosporin chemistry.
Claims7
A process for preparing a compound of the formula ##STR3## wherein Ar represents mono- or dicyclic aryl in which the cyclic groups are 5 or 6 membered or a heterocyclic group selected from pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, triazolyl, oxatriazolyl, thiatriazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl or indolyl, said aryl and heterocyclic groups being unsubstituted or substituted by halogen, hydroxy, C.sub.1 to C.sub.3 alkyl, alkoxy or alkanoyloxy,
- tet is tetrazolyl which is unsubstituted or substituted by C.sub.1 to C.sub.4 alkyl or C.sub.1 to C.sub.4 alkyl substituted by carboxy, esterified carboxy, cyano or dimethylamino,
- B.sup.1 and B.sup.2 independently represent a carboxy protecting group capable of being introduced into or removed from the molecule under conditions which do not have an adverse effect on the other portions of the molecule, which comprises subjecting a compound of the formula ##STR4## to epimerization with a base selected from the group consisting of alkali metal hydrogen carbonate, tri-lower alkylamine, diethanolamine, triethanolamine, pyridine, picoline, lutidine or collidine and subsequently precipitating the product.
Dependencies are inferred from the claim text.