New Synthetic Procedure of Semisynthetic Penicillin. I. : Studies on the Acyl Group Exchange of Natural Penicillin

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Other Title
  • 合成ペニシリンの新合成法に関する研究(第1報) : 天然ペニシリンのアシル基交換
  • 天然ペニシリンのアシル基交換
  • テンネン ペニシリン ノ アシルキ コウカン

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Description

3, 5-Di-tert-butyl-4-hydroxybenzyl benzylpenicillinate (IV) and trityl benzylpenicillinate (IX) were synthesised as a valuable intermediate in the chemical preparation of semisynthetic penicillins. These benzylpenicillin esters were treated with PCl5 and followed by methanol to form iminoethers. The iminoether (VI) derived from IV was allowed to react with 3-o-chloroplienyl-5-methylisoxazole-4-carbonyl chloride directly affording 3', 5'-di-tert-butyl-4'-hydroxybenzyl 3-o-chlorophenyl-5-methyl-4-isoxazolyl-penicillinate (VII) which was converted to cloxacillin (VIII) under mild basic conditions. The reaction of the iminoether derived from IX with D (-)-α-phenylglycyl chloride hydrochloride afforded α-aminobenzylpenicillin (X) after treatment of the reaction mixture with water. Several other semisynthetic penicillins were also obtained from IV and IX by this new procedure.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 92 (4), 454-458, 1972

    The Pharmaceutical Society of Japan

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