.ALPHA.,.BETA.-Unsaturated carboxylic acid derivatives. XI. Convenient synthesis of tert-butyl 2-alkoxy- and hydroxy-2-acetylamino-3-mono- or 3,3-dihaloalkanoates.

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概要

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• It was found that the halogenation of <I>t</I>-butyl 2-acetylamino-3-bromo-2-alkenoate (<B>3</B>) by NBS or NCS gave <I>t</I>-butyl 2-acetylimino-3,3-dihaloalkanoate (<B>6</B> and <B>7</B>). The addition of water or several saturated, unsaturated and polyhydric alcohols to the carbon-nitrogen double bond of <B>6</B> or <B>7</B> was accomplished to give <I>t</I>-butyl 2-acetylamino-2-alkoxy- and hydroxy-3,3-dihaloalkanoate. Similarly, the treatment of <I>t</I>-butyl 2-bromoacetylamino-2-alkenoate in alcohol gave <I>t</I>-butyl 2-acetylamino-2-alkoxy-3-bromoalkanoate, <I>via</I> the addition of alcohol to the imino intermediate (<B>2</B>). The formation mechanism and the structural assignment are discussed.

• 公益社団法人 日本化学会の論文

著者

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

• Sato Yoshiaki

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

• Shin Chung-gi

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

関連論文

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