Racemic structure and optical resolution by preferential crystallization of DL-cysteine salts of substituted benzenesulfonic acids.

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概要

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• Infrared absorption spectrum, solubility, and thermodynamic analysis indicated that DL-cysteine salts of benzenesulfonic acid (DL-BA salt) and 4-ethylbenzenesulfonic acid (DL-4-EB salt) are conglomerates at room temperature, but DL-BA salt forms a racemic compound at the melting point. These DL-salts were optically resolved by the preferential crystallization. As for DL-4-EB salt, suitable conditions were estimated by the free energy of critical nucleation in supersaturated solutions. The successive preferential crystallization in ethanol at 20 °C was found to give D- and L-4-EB salts with optical purity of 97–100% in the resolution yield of 83–90%. Purification and following treatment with triethylamine gave optically pure D- and L-Cys's.

• 公益社団法人 日本化学会の論文

著者

• KUROKAWA Hidemoto

  Faculty of Engineering and High Technology Research Center, Kansai University

• Shiraiwa Tadashi

  Faculty Of Chemistry Materials And Bioengineering Kansai University

• Sado Yujin

  Faculty of Engineering, Kansai University

• Sunami Michio

  Faculty of Engineering, Kansai University

• Tazoh Hirohide

  Faculty of Engineering, Kansai University

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