METHODS AND INTERMEDIATE COMPOUNDS FOR PRODUCING STERIC COMPOUNDS Russian patent published in 2013 - IPC C07C231/20 C07C231/02 C07C247/06 C07C237/04 C07D303/48 C07D301/02 C07D301/14 C07D301/19 

FIELD: chemistry.

SUBSTANCE: invention relates to methods of producing compounds of formula iii and an optically enriched salt of the compound of formula iii, where R₁ is C₁-C₆ alkyl; R'₁ is hydrogen; R'₂ is -NHR₂; R₂ is C₃-C₆ cycloalkyl. The methods are realised by oxidising an unsaturated compound of formula i , where the oxidant is tert-butylhydroperoxide, a mixture of samarium (III) isopropoxide, triphenyl arsine oxide, S-(-)1,1'-bi-2-naphthol and 4 Ǻ molecular sieves, or urea-hydrogen peroxide in the presence of trifluoroacetic anhydride to obtain a compound of formula ii ; and further reaction of the compound of formula ii with an amination agent, where the amination agent is an azide salt, and the intermediate azide-compound is reduced by hydrogenation to obtain a compound of formula iii. By reacting the compound of formula iii with an optically active organic acid selected from L-tartaric acid, malic acid, diisopropylidene gulonic acid and deoxycholic acid in a solvent, a salt of the compound of formula iii is obtained; and said salt is crystallised to obtain the same salt with more than 55% enantiomeric excess. The invention also relates to compounds: N-cyclopropyl-3-propyloxirane-2-carboxamide; 3-azido-N-cyclopropyl-2-hydroxyhexanamide; 3-amino-N-cyclopropyl-2-hydroxyhexanamide, salt of L-tartaric acid; 3-amino-N-cyclopropyl-2-hydroxyhexanamide, salt of deoxycholic acid.

EFFECT: improved methods of producing compounds of formula iii and an optically enriched salt of a compound of formula iii, novel intermediate compounds for producing serine protease inhibitors.

29 cl, 2 dwg, 14 ex