METHOD FOR PREPARING 5-(4-FLUOROPHENYL)-1-[2-(2R,4R)-4-HYDROXY-6-OXOTETRAHYDROPYRAN-2-YL)ETHYL]-2-ISOPROPYL-4-PHENYL-1H-PYRROL-3-CARBOXYLIC ACID PHENYLAMIDE Russian patent published in 2006 - IPC C07D405/06 

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for preparing 5-(4-fluorophenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxotetrahydropyran-2-yl)ethyl]-2-isopropyl-4-phenyl-1H-pyrrol-3-carboxylic acid phenylamide of the formula (I): . Method involves: (A) contacting compound of the formula (II) with transient-base metal as a catalyst, hydrogen source and a base in solvent medium to form compound of the formula (III): wherein R¹ represents -XR wherein X represents oxygen atom (O), sulfur atom (S) or selenium atom (Se), or R¹ represents -NR²R³ wherein each R² and R³ represents independently alkyl, cycloalkyl, arylalkyl or aryl, or R² and R³ taken in common represent -(CH₂)₄-, -(CH₂)₅-, -(CH(R⁴)-CH₂)₃-, -(CH(R⁴)-CH₂)₄-, -(CH(R⁴)-(CH₂)₂-CH(R⁴)-, -(CH(R⁴)-(CH₂)₃-CH(R⁴)-, -CH₂-CH₂-A-CH₂-CH₂-, -CH(R⁴)-CH_2-A-CH₂-CH₂-, -CH(R⁴)-CH₂-A-CH₂-CH(R⁴)- wherein R⁴ represents alkyl comprising of from one to four carbon atoms; A represents oxygen atom (O), sulfur atom (S), -NH or -NR wherein R represents alkyl, aryl, arylalkyl or heteroaryl; (b) conversion of compound of the formula (III) wherein R¹ is given above to compound of the formula (IV) with using a base in an aqueous methanol medium, and (c) contacting compound of the formula (IV) with acid in solvent medium to form compound of the formula (I). Invention provides the development of safety and effective method for synthesis of 5-(4-fluorophenyl)-1-[2-((2R,4R)-4-hydroxy-6-oxotetrahydropyran-2-yl)ethyl]-2-isopropyl-4-phenyl-1H-pyrrol-3-carboxylic acid phenylamide for the large-scale production.

EFFECT: improved preparing method.

13 cl, 2 ex