Issue 0, 1968

Studies related to penicillins. Part I. 6-α-Chloropenicillanic acid and its reaction with nucleophiles

Abstract

The preparation of 6-α-chloropenicillanic acid from the deamination of 6-β-aminopenicillanic acid has been improved, and the reaction is shown to proceed by way of 6-azopenicillanic acid. Benzyl 6-azopenicillanate has been isolated from the reaction of benzyl 6-β-aminopenicillanate with nitrous acid. Methyl 6-α-chloropenicillanate is rearranged to 6-azidocarbonyl-2,3-dihydro-3S-methoxycarbonyl-2,2-dimethyl-1,4-thiazine with sodium azide in NN-dimethylformamide and to 2,3-dihydro-3S,6-dimethoxycarbonyl-2,2-dimethyl-1,4-thiazine with methanolic sodium methoxide. 6-α-Chloropenicillanic acid undergoes similar rearrangements.

Article information

Article type
Paper

J. Chem. Soc. C, 1968, 2533-2537

Studies related to penicillins. Part I. 6-α-Chloropenicillanic acid and its reaction with nucleophiles

I. McMillan and R. J. Stoodley, J. Chem. Soc. C, 1968, 2533 DOI: 10.1039/J39680002533

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