METHOD FOR OBTAINING 5'-O-(3-PHENYLPROPIONYL)-N4-HYDROXYCYTIDINE Russian patent published in 2023 - IPC C07H19/67 C07D405/04 

FIELD: chemistry; pharmaceuticals; medicine.

SUBSTANCE: invention relates to a method for obtaining a new chemical compound, a derivative of N4-hydroxycytidine, which can be used to inhibit the replication of RNA and DNA-containing viruses (coronavirus, arbovirus). The invention relates to the field of organic chemistry and pharmaceuticals, and in particular to a method for obtaining a new derivative of N4-hydroxycytidine, which can be used to inhibit the replication of RNA and DNA-containing viruses. Disclosed is a method for preparing 5'-O-(3-phenylpropionyl)-N4-hydroxycytidine fromβ -D-N4-hydroxycytidine, including: (a) blocking vicinal 2' and 3' hydroxyl groups with acetonide protection to give intermediate 5'-O-(3-phenylpropionyl)-N4-hydroxycytidine; (b) blocking the hydroxyl group in 4' the position of N4-hydroxycytidine with a trityl protecting group to give the intermediate N4-trityloxy-2',3'-O-isopropylidenecytidine; (c) reaction of N4-trityloxy-2',3'-O-isopropylidenecytidine with phenylpropionic acid in the presence of 1,3-dicyclohexylcarbodiimide in methylene chloride to give the intermediate 3-phenylpropionic acid 2,2-dimethyl-6-(2- oxo-4-trityloxyamino-2H-pyrimidin-1-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl methyl ester; (d) acid hydrolysis of the 3-phenylpropionic acid intermediate 2,2-dimethyl-6-(2-oxo-4-trityloxyamino-2H-pyrimidin-1-yl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl methyl ester to form 5'-O-(3-phenylpropionyl)-N4-hydroxycytidine.

EFFECT: obtaining a new ester derivative of N4-hydroxycytidine with carboxylic acid in high yield.

4 cl, 6 dwg, 5 ex