IL40897A - Process for preparing 7-amino cephalosporanic acid derivatives - Google Patents

Claims (1)

1. IMS In a process for preventing reversion of an imino halide of a ester to a ester starting material during treatment of the imino halide with an alcohol or thiol when preparing acid the improvement which comprises reacting the imino halide in an inert organic liquid diluent in the presence of hydrogen halide with alcohols or thiols of the I II or z wherein X is oxygen or each of Y and Z is such that the alcohol or thiol has from 4 to about 12 carbon Y and Z are taken together with the carbon atom to which they are bonded to denote a cycloalkyl or when X is oxygen group having from to 8 ring forming carbon each of and is hydrogen or to and each of is hydrogen or a hydrocarbon such that the has from 3 to about carbon and each of and is hydrogen or such that the molecule has from 2 to about 12 carbon The process of claim wherein the pounds of formula I are The process of claim wherein the pounds of formula II or III are A process as defined in claim wherein the is reacted with from 3 to 6 moles of a disubstituted primary aliphatic alcohol or thiol of A process as claim wherein the primary aliphatic alcohol is isobutanol or 2 A process as defined in claim wherein the imlno halide reactant is the imlno chloride of amidodesacetoxycephalosporin ester obtained by treating with phosphorus pentachlorlde in the presence of a base a ester obtained by the ring expansion of a penicillin sulfoxide process as defined in wherein the imlno chloride of the ate ester is the imino chloride of or benzyl to form as product In ε process for preparing crystalline nltrobenzyl the which comprises reacting the imino chloride of a with from about 3 to about 6 moles of isobutanol per mole of imino or with from about 2 to 3 moles of a pound of formula II or III as defined in claim in an organic liquid in the presence of hydrogen The process of claim wherein the butanol is pounds of II or III is The process as defined in claim wherein the the imino of nitrobenzyl A as defined in claim wherein the imino chloride reactant is the imino chloride of nitrobenzyl A process for preparing a ester hydrohalide which comprises acting an imino halide of a sporinate ester in an organic liquid solvent in the presence of hydrogen halide with an alcohol or thiol the improvement which comprises selecting an alcohol or thiol of the formulae II or III as defined in claim The process of claim wherein the pounds of formula I are The process of claim wherein the pounds of formula II or III are as defined in claim wherein the imino halide reacted with from 3 to 6 moles of a primary aliphatic alcohol or A process as defined in wherein the primary aliphatic alcohol is A process as defined in wherein the imino halide reactant is the imino of a acylamidodesacetoxycephalosporinate obtained b treating with phosphorus pentaohlorlde in the presence of a base a ester tained by the ring expansion of a penicillin sulfoxide A process as defined in claim wherein the imino chloride of the sporinate ester is the imino chloride of 7 c8rboxylate form product o enzyl te A process defined in claim wherein the chloride of the sporlnate ester is the chloride to form as product r carboxylate The process claim 3 wherein the diol or thiol has the formtula 22 A process as defined in claim wherein the beta diol is 23 A process as defined in claim herein the diol has the formula as in claim A process as defined in claim wherein the imino halide is contaqted with from 2 to 3 moles of the compounds per mole of the imino chloride reactantf The process of wherein a pound of formula II or III is reacted with the imino chloride of benzyl or 3 form The process of wherein the lected imino halide is reacted with from 2 to 3 moles from a beta diol or thiol of the formula The process of claim wherein the lected ha reacted with 2 tp 3 moles of an alpha dlol or thiol of formula for insufficientOCRQuality