METHOD OF PRODUCING 5R-[(BENZYLOXY)AMINO]PIPERIDINE-2S-CARBOXYLATE AND OXALATES THEREOF Russian patent published in 2020 - IPC C07D211/60 

FIELD: chemistry.

SUBSTANCE: invention relates to methods of producing 5R-[(benzyloxy)amino]piperidine-2S-carboxylate and its oxalate, where L-glutamic acid or sodium salt of L-glutamic acid as a starting material is reacted with monochloroacetic acid under alkaline conditions by a substitution reaction to obtain N-carboxymethyl-L-glutamic acid (compound III), then compound III is reacted with an alcohol in the presence of an acid reagent through an esterification reaction to obtain a diester of N-alkoxycarbonylmethyl-L-glutamic acid (compound IV), under action of a strong base, compound IV is subjected to intramolecular condensation to form a ring, hydrolysis with decarboxylation and esterification to obtain piperidin-5-one-2S-carboxylate (compound V), compound V is condensed with a hydrochloride salt of benzyloxyamine in the presence of an alkali to obtain 5-[(benzyloxy)imino]piperidine-2S-carboxylate (compound VI), compound VI is subjected to reduction and chiral separation to obtain 5R-[(benzyloxy)amino]piperidine-2S-carboxylate (IIb) oxalate, which is then neutralized to obtain 5R-[(benzyloxy)amino] piperidine-2S-carboxylate (IIa). Obtained 5R-[(benzyloxy)amino]piperidine-2S-carboxylate (IIa) or oxalate 5R-[(benzyloxy)amino]piperidine-2S-carboxylate (IIb) is used to obtain avibactam (I).

EFFECT: use of an inexpensive and readily available starting material which is characterized by high selectivity and is environmentally friendly and environmentally friendly during the production process.

10 cl, 3 dwg, 17 ex