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Chemical studies of potential relevance to penicillin hypersensitivity. The synthesis of dl ‐2‐phenoxymethylpenicillenic acid and of dl ‐2‐(2,6‐dimethoxyphenyl)penicillenic acid
Author(s) -
Dudley Kenneth H.,
Bius Daniel L.,
Johnson Dorothy
Publication year - 1973
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570100609
Subject(s) - chemistry , oxazolone , hippuric acid , penicillin , chloride , penicillamine , acetyl chloride , medicinal chemistry , mercury (programming language) , organic chemistry , nuclear chemistry , urine , catalysis , antibiotics , biochemistry , computer science , programming language
Crystalline samples of DL‐2‐phenoxy melhylpenicillenic acid ( 14 ) and of DL ‐2‐(2, 6‐dimethoxyphenyl)penicillenic acid ( 21 ) have been synthesized by the reaction of DL ‐penicillamine with 2 phenoxymethyl‐4‐(methoxymethylene)oxazol‐5‐one and 2‐(2, 6‐dimethoxyphenyl)‐4‐(ethoxymethylene)oxazol‐5‐one, respectively. These key oxazol‐5‐one intermediates were synthesized by azlactonization of the appropriately substituted penaldic acid dialkyl acetals. The reaction of mercury(II) chloride with D‐phenoxymethylpenicillin was studied and found to be inapplicable to the synthesis of D‐14 . A comparison of crystalline DL ‐ and of amorphous D‐2‐(2,6‐dimethoxyphenyl)penicillenic acid (21), which were prepared by the “oxazolone” and “mercury(11) chloride” methods, respectively, suggests a marked improvement in the purity of the DL ‐material.