Racemic structures and optical resolutions by preferential crystallization of organic ammonium salts of N-formyl-DL-phenylalanine.

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概要

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• Racemic structures of the butylammonium salt, pentylammonium salt, benzylammonium salt, dicyclohexylammonium salt(DL-DCH salt), and 4-methylpiperidinium salt(DL-4-MP salt) of <I>N</I>-formyl-DL-phenylalanine were studied to explore the possibility of optical resolution by preferential crystallization. Free energies of formation of racemate (Δ<I>G</I><SUP>F</SUP>) of the DL-salts and data at eutectic points in binary phase diagrams of melting points indicate that the DL-salts form racemic compounds in the vicinity of the melting points. However, according to Δ<I>G</I><SUP>F</SUP> of DL-DCH and 4-MP salts and infrared spectra and solubilities of the DL- and L-salts, these DL-salts transform into conglomerates around room temperature. It is possible to resolve DL-DCH and 4-MP salts by preferential crystallization at 10 °C. Successive preferential crystallization of DL-4-MP salt at 10 °C in 1-butanol gives the D- and L-salts with optical purities of 95–100%.

• 公益社団法人 日本化学会の論文

著者

• Sakamoto Yoshihiro

  Faculty Of Engineering Musashi Institute Of Technology

• KUROKAWA Hidemoto

  Faculty of Engineering and High Technology Research Center, Kansai University

• MIYAZAKI Hideya

  Faculty of Engineering, Kansai University

• Shiraiwa Tadashi

  Faculty Of Chemistry Materials And Bioengineering Kansai University

• Sakamoto Yoshihiro

  Faculty of Engineering, Kansai University

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