MONO AND DIFLUOROSUBSTITUTED ETHYL (3R,4R,5S)-5-AZIDO-4-ACETYLAMINO-3-(1-ETHYLPROPOXY)-CYCLOHEXENE-1-CARBOXYLATES, METHOD OF OBTAINING AND APPLICATION Russian patent published in 2014 - IPC C07C247/14 C07C279/16 C07C237/02 A61P31/16 

FIELD: chemistry.

SUBSTANCE: invention relates to a novel method of obtaining alkyl (3R,4R,5S)-5-azido-3-(1-ethylpropoxy)-4-(mono or difluoro acetylamino)-cyclohex-1-enecarboxylates of general formula 1 and to a method of their application as half-products in synthesis of a nueramidase inhibitor of formula 18 In the said formulas R¹=H,F; R²=C₁-C₃-alkyl. The method of obtaining general formula 1 compounds consists of interaction of alkyl(3R,4R,5S)-5-azido-4-amino-3-(1-ethylpropoxy)-cyclohex-1-enecarboxylate with fluoro- or difluoroactic acid in tetrahydrofuran at room temperature in the presence of hydrochloride of N¹-((ethylamino)methylene)-N³, N³-dimethylpropane-1,3-diamine, 1H-benzo[d][1,2,3]triazol-1-ol and N-ethyl-N-isopropylpropane-2-amine. A compound 18 is obtained by reduction of the compound of general formula 1 with triphenylphosphine in aqueous tetrahydrofuran with the following interaction of the obtained compound with di-Boc-thiourea, hydrolysis of the obtained compound with lithium hydroxide in water dioxane and release of Boc-protection from the obtained acid with 30% solution of trifluoroacetic acid in methylene chloride.

EFFECT: obtaining intermediate products of general formula with application in the claimed method of the said reagents and conditions of reaction makes it possible to carry out the process more purposefully, reduce the quantity of side products and in that way simplify the process of obtaining and separation of the compounds.

4 cl, 5 ex