Synthesis of enantiomerically pure substituted (quinolin 2-ylmethoxy)phenyl acetic acid

PURPOSE: To obtain an enantiomerically pure substituted (quinolin-2yl-methoxy) phenyl acetic acid as an inhibitor of enzymatic reaction by stereoselectively alkylating a novel compound obtained from a hydroxyphenyl acetic acid derivative and a halogenomethyl quinoline and then, hydrolyzing with an acid. CONSTITUTION: The compound expressed by formula IV (e.g. (2R)2-(4(quinol-2yl- methoxy)phenyl2-cyclopentyl acetic acid expressed by formula V or the like) is obtained by stereoselectively alkylating a novel compound (e.g. a compound expressed by formula II or the like) expressed by formula I (each of A-G and L represents H, OH, a halogen, carboxyl, nitro, CF 3 , an aryl or the like and R 2 represents an alcohol residue having an asymmetric carbon) with the compound (e.g. bromocyclopentane) expressed by the formula, R 1 -Y (Y represents I, Br or the like and R 1 is a cycloalkyl) in an inert solvent in the presence of a base to produce a compound expressed by formula III and then, removing the residual group R 2 with an acid without racemizing. COPYRIGHT: (C)1993,JPO