3-Alkoxycarbonyl-2-oxazolones and Their Homopolymers as Highly Preservable Amino-Protecting Reagents. tert-Butoxycarbonylation and Benzyloxycarbonylation of Amino Groups

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概要

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• Highly preservable amino protecting reagents derived from the 2-oxazolone moiety as a common activating mediator have been developed. 3-Alkoxycarbonyl-2-oxazolones serve as easily handled reagents for amino protection, including tert-butoxycarbonylation, benzyloxycarbonylation, p-methoxybenzyloxycarbonylation, methoxycarbonylation and ethoxycarbonylation. For example, high yield N-protection of α-amino acids has been smoothly performed by the use of 3-tert-butoxycarbonyl [Boc-Ox] and 3-benzyloxycarbonyl-2-oxazolones [Cbz-Ox] in aqueous solution at room temperature. A series of homopolymers, poly (3-alkoxycarbonyl-2-oxazolone), is readily obtainable by radical-initiated chain reaction of the corresponding 4,5-unsubstituted oxazolone monomers (except for the tert-butoxy derivative, which failed to give polymeric compounds), and these were successfully used for amino protection as well. Use of the polymer reagents greatly simplifies the purification procedure, though a longer reaction time is required.

• 公益社団法人日本薬学会の論文
• 1984-06-25

著者

• 広部 雅昭

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 国枝 武久

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 樋口 恒彦

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 樋口 恒彦

  東京大学薬学部

• 広部 雅昭

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 広部 雅昭

  東京大学薬学部:文部省

• 国枝 武久

  Faculty Of Pharmaceutical Sciences Kumamoto University

• 国枝 武久

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 阿部 芳広

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 阿部 芳広

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 樋口 恒彦

  Waseda Univ.

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