3-Amino-3-methyl-2-azetidinone-1-sulfonic Acidおよびその誘導体の合成

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概要

• 論文の詳細を見る

• N-Benzyloxy-2-(N-tert-butoxycarbonyl) amino-2-hydroxymethylpropionamide (8) was synthesized from methyl DL-isocyanopropionate (2). Compound 8 was treated with diethyl azodicarboxylate and triphenylphosphine to give β-lactam derivative (9), which was hydrogenolized with H_2/Pd-C to the N-hydroxy compound (10) followed by treatment with TiCl_3 to give the unsubstituted β-lactam derivative (11). Sulfonation of 11 with a pyridine-sulfur trioxide complex and deprotection with formic acid afforded a key intermediate, DL-3-amino-3-methyl-2-azetidinone-1-sulfonic acid (12). The desired 3-N-acylamino-3-methyl-2-azetidinone-1-sulfonic acid derivatives (13a, 13c and 13e) were obtained by acylation of 12. None of the compounds (13a, 13c and 13e) showed antibacterial activity, although the 4α-methyl counterparts (13f) had some activities against gram-negative bacteria.

• 公益社団法人日本薬学会の論文
• 1983-11-25

著者

• 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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