A new synthesis of ampicillin and related investigations |
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| Authors: | F. Kajfe ,T. Kova
,M. Mihali&#x ,B. Belin,V. &#x unji&#x |
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| Affiliation: | F. Kajfež,T. Kovač,M. Mihalić,B. Belin,V. Šunjić |
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| Abstract: | Quaternization of (S)-α-bromophenylacetic acid amide (8) with hexamethylentetramine (hexamine) preceded with ca. 80% inversion of configuration. Accordingly, starting from the trimethylsilylester of N-(S)-(α-bromo-α-phenylacetyl)-6-aminopenicillanic acid (4) quaternization with hexamine and subsequent hydrolysis afforded N-(R)-α-phenylglycyl-6-aminopenicillanic acid (1, ampicillin). Some other model reactions have been investigated. |
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