PURPOSE: To obtain the titled compound useful as an anti-inflammatory agent, industrially and advantageously, by the reaction of a novel propionic acid ester derivative with sulfur and a secondary amine, and the subsequent hydrolysis and then the cyclization of the hydrolysis product in the presence of a condensing agent.
CONSTITUTION: A novel compound of formula I (Z is O or S; R1 is lower alkyl) is reacted with sulfur and a secondary amine of formula II (R2 and R3 are lower alkyls or a heterocyclic ring with the N adjacent), for example, under the usual Willgerodt-Kindler reaction conditions, to prepare the compound of formula III, which is hydrolyzed by the conventional method to give a dicarboxylic acid of formula IV. The resulting compound is cyclized in the presence of a condensing agent, e.g. polyphosphoric acid, which is applied to the intramolcular acylation, to give a propionic acid derivative of formula V. This reaction is suitable for an industrial process because of high yield and less reaction stages than the conventional ones and no dangerous reaction.
NAGAI YASUTAKA