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

概要

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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 PCl_5 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.
公益社団法人日本薬学会の論文
1972-04-25