METHOD OF PRODUCING ALKYL 2-[([1,1'-BIPHENYL]-4-CARBONYL)AMINO]-3-(1H-AZOL-1-YL) PROPANOATES Russian patent published in 2020 - IPC C07D233/61 C07D249/02 

FIELD: chemistry.

SUBSTANCE: invention relates to organic chemistry and specifically to a method of producing alkyl 2-[([1,1'-biphenyl]-4-carbonyl)amino]-3-(1H-azol-1-yl) propanoates of general formula I

,

where R denotes an imidazole or triazole heterocyclic moiety, R1 denotes alkyl groups of a straight or branched structure with 1 to 4 carbon atoms. Method, which comprises condensing carboxylic acid 4-biphenyl acid chloride with L-serine alkyl ester hydrochloride in aprotic polar solvent, acetonitrile in presence of triethylamine to obtain alkyl 2-[([1,1'-biphenyl]-4-carbonyl)amino]-3-hydroxypropanoate, the obtained amide is converted into an oxazoline derivative in an aprotic nonpolar solvent in presence of 20-21-fold molar excess of thionyl chloride at 0–5 °C. Further, alkyl 2-([1,1'-biphenyl]-4-yl)-4,5-dihydro-1,3-oxazole-4-carboxylate is disclosed by imidazole or triazole in presence of 1–1.001 mol% of zinc chloride at temperature of 145–150 °C without a solvent in melt for 20–30 hours to obtain the desired compound of formula I.

EFFECT: technical result: novel method of producing alkyl 2-[([1,1'-biphenyl]-4-carbonyl)amino]-3-(1H-azol-1-yl) propanoate, having a higher yield of the product and being a cheaper method.

1 cl, 3 tbl, 10 ex