7-アミノデアセトキシセファロスポラン酸の脱硫反応

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概要

• 論文の詳細を見る

• The Raney nickel desulfurization of 7-aminodeacetoxycephalosporanic acid (7-ADCA) was investigated to obtain 2-(3-amino-2-oxo-1-azetidinyl)-3-methyl-2-butenoic acid derivative (3a), a useful intermediate in a synthesis of monobactam compounds. The desulfurization of 7-ADCA gave a monocyclic β-lactam 3a and an unexpected 5-oxazolone derivative 5a. Compound 5a would be formed by the lactonization of alanyldehydrovaline derivative 4 derived from the hydrogenolytic cleavage of N-C^4 bond of β-lactam ring in 7-ADCA. Similarly the desulfurization of cephalexin with Raney nickel gave the monocyclic β-lactam 3b and the 5-oxazolone derivative 5b. Compound 3a on treatment by the reported procedure gave 3-amino-2-azetidinone-1-sulfonic acid (7). Monobactam compounds 8 were obtained by acylation or arylation of 7. None of compounds 8a-e showed in vitro antibacterial activity against gram-positive and -negative bacteria.

• 公益社団法人日本薬学会の論文
• 1984-03-25

著者

• 廣瀬 徹

  大日本製薬株式会社 総合研究所

• 広瀬 徹

  Research Laboratories Dainippon Pharmaceutical Co. Ltd.

• 千葉 勝已

  大日本製薬株式会社総合研究所

• 三塩 晋作

  大日本製薬株式会社 総合研究所

• 中野 純次

  大日本製薬株式会社 総合研究所

• 宇野 準

  大日本製薬株式会社総合研究所

• 中野 純次

  Exploratory Research Laboratories, Dainippon Pharmaceutical Company, Ltd.,

• 宇野 準

  大日本製薬株式会社

• 中野 純次

  Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.

• 中野 純次

  大日本製薬株式会社総合研究所

• 宇野 準

  大日本製薬

• 宇野 準

  Research Laboratory Dainippon Pharmaceutical Co. Ltd.

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