24 イオン交換樹脂上での加水分解反応 : γ-アミノ-β-ヒドロキシブタン酸およびその関連化合物の合成
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The hydrolysis of esters, amides, nitriles and proteins by ion exchange resins as a catalyst has been reported in several recent publications. The new procedure of hydrolysis on ion exchange resins and its application to the synthesis of γ-amino-β-hydroxybutanoic acid will be discussed. The new technique was developed on the basis of the thought that the compounds absorbed on ion exchange resin should be easily hydrolyzed. Because the hydrolyzing functional groups of the compound on the resin are inevitably quite closed to the catalytic function of the resin. Therefore, this kind of the reaction could be a crude model of enzymatic hydrolysis. γ-Aminobutanoic acid amides (2, 11, 12) were hydrolyzed on cation exchange resin Amberlite IR-12OB to the mother amino acid (7). Not only succinic acid mono-methyl ester (13) and succinic acid amides (14, 15) but also N-acetyl-γ-aminobutanoic acid (17) were hydrolyzed on anion exchange resin Amberlite IRA-400. γ-Amino-β-hydroxybutyronitrile (19) and its N-trimethyl derivative (20) were also hydrolyzed on Amberlite 252. As a application of this technique, γ-amino-β-hydroxybutanoic acid (GABOB) (22) was simply synthesized from γ-chloro-β-hydroxybutyronitrile (30) by three steps (the over-all yield: 65 %). Especially, the synthesis was characterized by using the same resin in order to purify and hydrolyze the intermediate amine-amide (24) at the only one process.
- 天然有機化合物討論会の論文
- 1973-10-01
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