Asymmetric transformation of DL-p-hydroxyphenylglycine by a combination of preferential crystallization and simultaneous racemization of the o-toluenesulfonate.
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概要
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The asymmetric transformation of DL-<I>p</I>-hydroxyphenylglycine was achieved between two enantiomers by a combination of preferential crystallization of a desired enantiomer of <I>p</I>-hydroxyphenylglycine <I>o</I>-toluenesulfonate (HPG·<I>o</I>-TS) and the simultaneous racemization of the antipode. L-HPG·<I>o</I>-TS was easily racemized by heating at 100 °C in aqueous 95% (v/v) acetic acid in the presence of small amounts of salicylaldehyde and free DL-HPG. A supersaturated solution of DL-HPG·<I>o</I>-TS placed under such conditions for racemization was seeded with the crystals of D-HPG·<I>o</I>-TS, and added with DL-HPG and <I>o</I>-toluenesulfonic acid in order to provide continuously the supersaturated state of DL-HPG·<I>o</I>-TS as a driving force. As a result, 77.2% of DL-HPG added was transformed to D-isomer.
- 公益社団法人 日本化学会の論文
著者
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Chibata Ichiro
Research Laboratories Tanabe Seiyaku Co. Ltd.
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Yamada Shigeki
Research Laboratories Tanabe Seiyaku Co. Ltd.
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Yoshioka Ryuzo
Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
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Tohyama Masanori
Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
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Hongo Chikara
Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd.
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