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Paper | Regular issue | Vol 43, No. 1, 1996, pp.133-140
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7241
Absolute Configuration of Optical Isomers of 2-(4-Chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic Acid (Rebamipide)

Jun Matsubara, Kenji Otsubo, Seiji Morita, Tadaaki Ohtani, Yoshikazu Kawano, and Minoru Uchida*

*Tokushima Research Institute, Otsuka Pharmaceutical Co., Ltd., Kagasuno 463-10, Kawauchi-cho, Tokushima 771-01, Japan

Abstract

The absolute configuration of enantiomers of 2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid [(±)-1, rebamipide] was assigned. The key intermediate, (S)-quinoline derivative [(S)-3], was prepared by palladium-catalyzed coupling reaction of 4-iodoquinoline with organozinc compound. This quinolinylalanine derivative was also synthesized from α-amino acid derivative of 2(1H)-quinolinone [(+)-4], which was able to convert into optically active rebamipide. Therefore the absolute configuration of (+)- and (-)-rebamipide was found to be R and S, respectively.