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Base‐catalyzed hydrolysis of 6‐aminopenicillanic acid. The kinetic and thermodynamic products
Author(s) -
Carroll R. D.,
Jung S.,
Sklavounos C. G.
Publication year - 1977
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.5570140330
Subject(s) - chemistry , hydrolysis , sodium hydroxide , kinetic energy , catalysis , imine , hydroxide , proton nmr , hydrolysis constant , carbon 13 nmr , proton , organic chemistry , acid catalysis , base (topology) , kinetics , reaction rate constant , mathematical analysis , physics , mathematics , quantum mechanics
In the presence of sodium hydroxide or a β‐lactamase, 6‐APA has been shown to hydrolyze rapidly at room temperature to penicic acid 3 , the kinetic product of the reaction. In a subsequent equilibration 3 isomerizes at C‐5, by way of intermediate imine 4 , affording 5‐epi‐penicic acid 6 as the major hydrolysis product (∼ 95% at equilibrium). The pH and temperature parameters of equilibration are discussed and HPLC, optical rotation, proton nmr and 13 C nmr data are presented.