The optical resolution and asymmetric transformation of DL-p-hydroxyphenylglycine with (+)-1-phenylethanesulfonic acid.
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概要
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Optically active 1-phenylethanesulfonic acid was found to be an efficient resolving agent for the optical resolution and asymmetric transformation of DL-<I>p</I>-hydroxyphenylglycine. When DL-<I>p</I>-hydroxyphenylglycine was resolved by the fractional crystallization of its diastereomeric salt with (+)-1-phenylethanesulfonic acid, less soluble D-<I>p</I>-hydroxyphenylglycine (+)-1-phenylethanesulfonate [D-HPG·(+)-PES] was obtained in a good yield. Soluble L-HPG·(+)-PES was easily epimerized into DL-HPG·(+)-PES by heating it at 100 °C in glacial acetic acid in the presence of a small amount of salicylaldehyde. Under such epimerizing conditions, the asymmetric transformation of DL-HPG·(+)-PES was attempted by simultaneously combining the fractional crystallization of the less soluble D-HPG·(+)-PES and the epimerization of the soluble L-HPG·(+)-PES. This asymmetric transformation was achieved successfully; that is, 80% of the DL-HPG used as the starting material was converted into D-HPG.
- 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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Ohtsuki Osamu
Research Laboratory of Applied Biochemistry, 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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