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Degradation of clavulanic acid in aqueous alkaline solution isolation and structural investigation of degradation products



Degradation of clavulanic acid in aqueous alkaline solution isolation and structural investigation of degradation products



Chemical & Pharmaceutical Bulletin 33(1): 218-224



The degradation of potassium clavulanate [having antibacterial properties] in a weakly alkaline aqueous solution was investigated. Potassium clavulanate was degraded in 0.1 M Na2HPO4 solution at various temperatures. Four degradation products were isolated and their structures were elucidated as 2,5-bis(2-hydroxyethyl)pyrazine (I), 3-methyl-2,5-bis-(2-hydroxyethyl)pyrazine (II), 3-(2-carboxyethyl)-2,5-bis-(2-hydroxyethyl)pyrazine (III), and 3-ethyl-2,5-bis-(2-hydroxyethyl)pyrazine (IV) by mass spectroscopy and NMR spectroscopy. High-performanc liquid chromatographic analysis of the reaction solution indicated that the reaction at 60.degree. C yielded at 4 pyrazine derivatives; II was not formed at 35.degree. C and III was not formed at 100.degree. C. A reaction mechanism is proposed which involves 4-amino-3-oxobutanol (IX) as a key intermediate.

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Accession: 005099243

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DOI: 10.1248/cpb.33.218


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