METHOD OF PRODUCING INTERMEDIATE COMPOUND FOR PRODUCING AVIBACTAM Russian patent published in 2020 - IPC C07D471/08 

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry, specifically to a method of producing an intermediate compound for producing avibactam, which comprises the following steps: (1) compound of formula III is dissolved in solvent A, hydrolysed in presence of base A and then acidified to obtain compound of formula IV:

III IV,

where R in a compound of formula III denotes C_1-6-aliphatic group or -alkyl-substituted phenyl; preferably R is selected from a group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, tert-pentyl, hexyl, benzyl, o-methylbenzyl and p-methylbenzyl; (2) a compound of formula IV and solid phosgene or diphosgene are simultaneously added to a cyclisation reaction of urea and a chloroformylation reaction in the presence of an organic base B and a catalyst in solvent B to obtain a compound of formula V which is used directly at the next reaction step without purification;

V,

(3) an amidation reaction is carried out using a compound of formula V and ammonia to obtain (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide.

EFFECT: technical result is a method of producing, which is simple and suitable for use without the need for a special protective agent or reagent for carbonylation, and is environmentally friendly.

9 cl, 3 dwg, 9 ex