Preparation of Optically Active threo-2-Amino-3-hydroxy-3-phenylpropanoic Acid (threo-β-Phenylserine) via Optical Resolution

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  • Shiraiwa Tadashi
    Unit of Chemistry, Faculty of Engineering and High Technology Research Center, Kansai University
  • Saijoh Reiichi
    Unit of Chemistry, Faculty of Engineering and High Technology Research Center, Kansai University
  • Suzuki Masahiro
    Unit of Chemistry, Faculty of Engineering and High Technology Research Center, Kansai University
  • Yoshida Kyosuke
    Unit of Chemistry, Faculty of Engineering and High Technology Research Center, Kansai University
  • Nishimura Satoshi
    Unit of Chemistry, Faculty of Engineering and High Technology Research Center, Kansai University
  • Nagasawa Hisashi
    Unit of Chemistry, Faculty of Engineering and High Technology Research Center, Kansai University

書誌事項

タイトル別名
  • Preparation of Optically Active threo-2-Amino-3-hydroxy-3-phenylpropanoic Acid (threo-.BETA.-Phenylserine) via Optical Resolution
  • Preparation of Optically Active threo 2 Amino 3 hydroxy 3 phenylpropanoic Acid threo ベータ Phenylserine via Optical Resolution
公開日
2003
資源種別
journal article
DOI
  • 10.1248/cpb.51.1363
公開者
公益社団法人 日本薬学会

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説明

To obtain optically active threo-2-amino-3-hydroxy-3-phenylpropanoic acid (1), (2RS,3SR)-2-benzoylamino-3-hydroxy-3-phenylpropanoic acid [(2RS,3SR)-2] was first optically resolved using (1S,2S)- and (1R,2R)-2-amino-1-(4-nitrophenyl)-1,3-propanediol as the resolving agents to afford (2R,3S)- and (2S,3R)-2 in yields of 73% and 66%, based on half of the starting amount of (2RS,3SR)-2. Next, the racemic structures of ammonium and some organic ammonium salts of (2RS,3SR)-2 were examined based on melting point, solubility, and infrared spectrum, with the aim of optical resolution by preferential crystallization. The benzylammonium salt of (2RS,3SR)-2 was suggested to exist as a conglomerate at room temperature, although it forms a racemic compound at the melting point. The optical resolution by preferential crystallization of the racemic salt afforded the (2R,3S)- and (2S,3R)-salts with optical purities of 90—97%. The (2R,3S)- and (2S,3R)-2 obtained from the purified salts were hydrolyzed by reflux in hydrochloric acid to give (2R,3S)- and (2S,3R)-1.

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