A Practical Procedure for the Synthesis of Esonarimod, (R,S)-2-Acetylthiomethyl-4- (4-methylphenyl)-4-oxobutanoic Acid, an Antirheumatic Agent. II

Abstract

An efficient large-scale synthesis of Esonarimod, (R,S)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid (1), a new antirheumatic drug, was established. A small amount of water increased the yield of the Michael addition of thioacetic acid (4) to 2-methylene-4-(4-methylphenyl)-4-oxobutanoic acid (2) to give 1. Multikilogram amounts of 1 (over 25 kg) were successfully obtained using this procedure. In addition, this procedure was repeated nine times, and reproducible results were obtained.

See Ref. [1]

Keywords:

• Esonarimod
• Antirheumatic drug
• Friedel–Crafts acylation
• Michael addition
• Process chemistry

Notes

See Ref. [1]