- Synthetic Method of Zoliprofen
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Zoliprofen (CAS NO.: ), with its systematic name of 2-(4-(2-Thiazolyloxy)phenyl)propionic acid, could be produced through many synthetic methods.
Following is one of the reaction routes:
(I) is esterified by isopropanol and H2SO4 to produce the corresponding isopropyl ester (II), and the yielding product is then cyclocondensed with 1-isobutoxy-2-chloroethyl isothiocyanate (III) in the presence of K2CO3 in acetone giving isopropyl 2-[4-(4-isobutoxy-2-thiazolin-2-yloxy) phenyl]acetate (IV). Elimination of isobutanol from (IV) by means of p-toluenesulfonic acid in hot DMF affords isopropyl 2-[4-(2-thiazolyloxy)phenyl] acetate (V), which is methylated with methyl bromide and KOH in DMF giving isopropyl 2-[4-(2-thiazo)yloxy)phenyl]propionate (VI). At last, this compound is hydrolyzed with NaOH in aqueous methanol.
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