PROCESS FOR THE PREPARATION OF 2-(PRIMARY/SECONDARY AMINO)HYDROCARBYL)- CARBAMOYL-7-OXO-2,6-DIAZA-BICYCLO3.2.0.HEPTANE-6-SULFONIC ACID DERIVATIVES

摘要

A process for the production of a compound of formula(I) wherein A LINKER B represents a linker moiety of formula (V): A[G1- G2*- G3]B; wherein A and B indicate the orientation of the groupof formula (V) in formula (I); G1, G2 and G3 have specific meaningsdescribed herein and may be present or absent, with the proviso that atleast one of G1 or G3 is present; which linker group may furthermoreoptionally contain one or more groups of formula (VI); and/or othersubstituents; and R1 represents hydrogen or a C1-C4-alkyl group; R2represents hydrogen or a C1-C4-alkyl group; R3 independently at eachoccurrence, represents hydrogen or a C1-C4-alkyl group; x is 0 or 1; y is0 or 1; z independently at each occurrence, is 0 or 1; and (- -) representsa single bond between a primary, secondary or tertiary carbon atomof the moiety A LINKER B and the adjacent nitrogen atom; in whichprocess (A) a compound of formula (II) is reacted with a compound offormula (III) wherein Pr represents an amino protecting group selectedfrom t-butyloxy carbonyl (t-Boc), 1-methyl-1-(4-biphenylyl)ethyloxycarbonyl (Bpoc), 1-(1-adamantyl)-1-methylethyloxy carbonyl (Adpoc),1-(3,5-di-t-butylphenyl)-1-methyl ethyl oxy carbonyl (t-Bumeoc),1-adamantyloxy carbonyl (Adoc), p-methoxybenzyloxy carbonyl(Moz), o,p-dimethoxybenzyloxy carbonyl, A LINKER B has the samemeaning as in formula (I) with the exception that one or more of theoptional groups of formula (VII) may be replaced by a group of formula(VII) and R1; R2; R3; x; y; z and (--), at each occurrence, have thesame meaning as in formula (I) and Pr is as defined above; in a dipolaraprotic solvent in the presence of a base to obtain a compound offormula (IV) wherein Pr; A LINKER B; R1; R2; R3; x; y; z; and (- -), ateach occurrence, have the same meaning as in formula (III); which compound isthen (B) deprotected by reaction with formicacid or a mixture of formic acid or acetic acid with hydrochloric acid orhydrobromic acid, to give the compound of formula (I)as well as the compounds of the aforementioned formula (IV).