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Note | Regular issue | Vol 63, No. 3, 2004, pp.699-706
Published online, 16th January, 2004
DOI: 10.3987/COM-03-9972
■ Practical Synthesis of DQ-113, a New Quinolone Antibacterial Agent, by Using the Intramolecular Horner-Wadsworth-Emmons Reaction

Hiroaki Inagaki, Toshiyuki Takeda, Rie N. Miyauchi, Katsuhiro Kawakami, Hisashi Takahashi, and Makoto Takemura*

*Medicinal Chemistry Research Laboratory, Daiichi Pharmaceutical Co., Ltd., 16-13, Kita-Kasai 1-Chome, Edsogawa-ku, Tokyo 134-8630, Japan

Abstract

A practical route was developed for synthesizing the C-7 substituent of DQ-113 (6, 5-amino-7-[(3S,4R)-4-(1-aminocycloprop-1-yl)-3-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-1,4-dihydro- 8-methyl-4-oxoquinolin-3-carboxylic acid), a new quinolone antibacterial agent for serious infections caused by Gram-positive pathogens. The key step was the intramolecular Horner-Wadsworth-Emmons reaction. In addition, the yield of the final aromatic nucleophilic substitution reaction was improved.