ES362137A1 - A procedure to prepare acilpenicillines. (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

A procedure for preparing acylpenicillins of the formula **(See formula)** in which M is selected from the group consisting of hydrogen, sodium, potassium or tri (lower alcohol) amine, which comprises reacting **(See formula)** with a compound of the formula **(See formula)** where it is thienyl, furyl, pyridyl, phenyl, or substituted phenyl where the substituent is lower alcohol, chloro, hromo, lower alkoxy, di- (lower alcohol) amino or trifluoromethyl; X'is -OR2 or -SR7 where R2 is hydrogen or sodium, phenyl or substituted phenyl where the substituent is at least one of the chlorine, bromine, fluoro, lower alcohol, lower alkoxy, lower alkanoyl, (carbo (alkoxy lower), nitro or di- (lower alcohol) amino; furyl, quinoline, methyl substituted quinoline, phenazinyl, 9,10-anthraquinonyl, phenanthrenquinoneyl, anthracenyl, phenanthril, (1,3-henzodioxolyl), 3- (2-methyl -4-pironil), 3- (4-pironil) or (N-methyl) pyridyl: **(See formula)** where Y2 is: **(See formula)** where Z'is lower alcoholic and is - (CH2) 3- and - (CH2) 4- or its substituted derivatives where the substituent is methyl, chlorine or bromine; benzyl, substituted benzyl in which the substituent is chlorine, bromine, fluoro, lower alcohol, lower alkoxy, lower alkanoyl, carbo (lower alkoxy), nitro and di (lower alcohol) amino; phthalimidomethyl, benzohydryl, trityl, cholesteryl, alkenyl having up to 8 carbon atoms, alkynyl having up to 8 carbon atoms, cycloalkyl or cycloalkyl substituted by (lower alcohol) having from 3 to 7 carbon atoms in the cycloalcoyl residue, bicyclo [4.4.0] decyl, tujyl, fenchyl, isophenyl, 7-adamantanyl, (2-pyrrolidone) methyl, (4-imidazolyl) methyl, 1-indanylmethyl, 2-indanylmethyl, (2-pyrrolidone) methyl, (4-imidazolyl) methyl, 1-indanylmethyl, 2-indanylmethyl, [2,2-di (lower alcohol) -1,3-dioxolon-4-yl] methyl, furylmethyl, pyridylmethyl, ac-indanyl or its substituted derivatives in which the substituent is methyl, chlorine, or bromine; ac-tetrahydronaphthyl and its substituted derivatives in which the substituent is methyl, chlorine or bromine; alcohol or substituted lower alcohol in which the substituent is at least one of the groups chloro, bromine, fluoro, nitro, carbo (lower alkoxy), lower alkanoyl, lower alkoxy, cyano, (lower alcohol) mercapto, (lower alcohol) sulfinyl, (lower alcohol) sulfonyl; **(See formula)** where -NR5R6, is -NH (lower alkanoyl), (see formula) in which the groups (lower alcohol) can be the same or different; and -N (lower alcohol) aniline; and Y1 is azetidine, aziridino, pyrrolidino, piperidino, morfolino, tio-morfolino, N- (lower alcohol) piperazino, pirrolo, imidazolo, 2-imidazolino, 2,5-dimetilpirrolidino, 1,4,5,6-tetrahidropirimidino, 4 -methylpiperidino or 2,6-dimethyl-piperidino; wherein each of the lower alkoxy, lower alcohol, or lower alkanoyl groups have 1 to 4 carbon atoms, and (lower alcohol) contains 1 to 3 carbon atoms; and R7 is hydrogen or sodium, phenyl, mono-di- or tri-substituted phenyl in which the substituent is at least one of the chlorine, bromine, fluoro, lower alcohol, lower alkoxy or trifluoromethyl groups, with the proviso that only one the ortho positions relative to the thio group of the phenyl moiety are substituted; wherein each of the lower alcohol and lower alkoxy groups contains from 1 to 4 carbon atoms, in a reaction inert solvent, at a temperature from about -70ºC to about 30ºC; and, if desired, when R2 is hydrogen or sodium, by treatment of compounds of formula I wherein R2 is benzyl or benzyl substituted by catalytic hydrogenation at room temperature, by hydrolysis with aqueous sodium carbonate, or by hydrolysis with weak acid . (Machine-translation by Google Translate, not legally binding)