ES419313A1 - Process for producing 7-amino and 7-acylamino-7-alkoxycephalo sporins - Google Patents

Abstract

A procedure for the preparation of 7-acylamido-7-alkoxycephalosporins of formula: **(See formula)** where Ro represents a C1-C4 primary lower alkyl or methyl-d3 group; R1 represents acetoxy, carbamoyloxy, α-methoxy-p-hydroxycinmoyloxy, propionyloxy, benzoyloxy, methoxy, methylthio, 1-ethyl-1,2,3,4-tetrazol-5-ylthio or 5-methyl-1,3,4- thiadiazol-2-ylthio; R2A represents hydrogen or R2; and R2 represents C1-C6-alkyl, 2,2,2-trichlorethyl, 2-iodoethyl, C5-C7-tert-alkenyl, C5-C7-tert-alkynyl, benzyl, ar-nitrobenzyl, tetrahydropyranyl, succinimidormethyl, phthalimidomethyl, ar-methoxybenzyl, ar, ar-dimethoxybenzyl, cyanomethyl, nitrophenyl, dinitrophenyl, 2,4,6-trinitrophenyl, bi- (p-methoxyphenyl) -methyl, triphenylmethyl, diphenylamethyl, benzyloxymethyl, alkanoyl (lower) oxymethyl C3-C6 or phenacyl; and R5 represents C1-C8 alkanoyl, axidoacetyl, cyanoacetyl, haloacetyl, (see formula) where Ar means phenyl, thienyl, furipyrrolyl or phenyl substituted with 1 to 3 substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, trifluoromethyl, protected amino, protected hydroxy, C1-C3 alkyl, C1- alkoxy C3, cyano and nitro; (see formula) where Ar'represents phenyl, pyridyl or substituted phenyl as defined above and Y is oxygen or sulfur; (see formula) where Ar is the one defined above and B is a protected amino group, hydroxy protected, carboxy protected, -CN or -N3; 2- (3-sidnon) acetyl or 2- (1H-tetrazol-1-yl) acetyl, by deacylation of an iminohalide of a 7-acylamidocephalosporin by reaction with an alcohol whose process is characterized by reacting an iminohalide compound of formula: **(See formula)** where X represents bromide or chloride; R1 is the one defined above; R2B represents R2 as defined above, C2-C4 lower alkanoyl or a radical of formula: **(See formula)** wherein each R3 group independently represents C1-C4 lower alkyl or halogen selected from the group consisting of bromine, chlorine, fluorine and iodine, with the limitation that at least one R3 group represents lower alkyl; and R4 represents an acylamido group where the acyl is C1-C4 alkanoyl, benzoyl, naphthoyl, C2-C5 alkoxycarbonyl, C6-C7 cycloalkoxycarbonyl, benzyloxycarbonyl, naphthyloxycarbonyl, one of the above groups substituted with one to three groups, each of them selected from the group consisting of halogen, nitro, C1-C4 lower alkoxy, cyano and, in the case of benzoyl, naphthoyl, benzyloxy and naphthyloxy, by lower alkyl C1-C4 or phthaloyl; with an alcohol of the formula Ro-OH, under essentially non-aqueous conditions; and reacting the product therefrom in situ with a compound of one of the formulas X-R5 and O - (- R5) 2 where X represents bromine or chlorine and R5 has the meaning given above. (Machine-translation by Google Translate, not legally binding)