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Reactions of mercapto amino acids

Communication 12. Acylation of 3-mercaptovaline with 2-(acylamino)acrylic acids and with 3-oxazolin-5-ones

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    The seven-membered heterocyclic compounds methyl 6-(acylamino)-2,2-dimethyl-5-oxo-1-thia-4-azacycloheptane-3-carboxylates were synthesized by the condensation of 3-mercaptovaline (3,3-dimethylcysteine) methyl ester with 2-(acylamino)acrylic acids, and by successive halogenation and dehydrohalogenation reactions these products were converted into new isomers of phenyl- and benzyl-penicillin: 2-(acylamino)-2,2-dimethyl-5 -oxo-1 -thia -5-aza-5-cycloheptene-3 -carboxylic acids.

  2. 2.

    It was shown that the isomerization of six-membered cyclic compounds into unsaturated seven-membered cyclic compounds can occur, the case studied being that of the conversion of methyl 6-(acylamino)-6-(halomethyl)-2,2-dimethyl-5-oxo-3-thiarnorpholinecarboxylates (XII) into methyl 6-(acylamino)-2,2-dimethyl -5 -oxo-1 -thia -4-aza-5-cycloheptene-3 -carboxylates (VII).

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences, USSR

    I. L. Knunyants, O. V. Kil'disheva, M. P. Krasuskaya, M. G. Lin'kova, V. V. Shokina, Z. V. Benevolenskaya & L. P. Rasteikene

Authors
  1. I. L. Knunyants
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  2. O. V. Kil'disheva
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  3. M. P. Krasuskaya
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  4. M. G. Lin'kova
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  5. V. V. Shokina
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  6. Z. V. Benevolenskaya
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  7. L. P. Rasteikene
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Additional information

We take the opportunity of thanking S.S. Dubov for the investigation of the infrared spectra.

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Knunyants, I.L., Kil'disheva, O.V., Krasuskaya, M.P. et al. Reactions of mercapto amino acids. Russ Chem Bull 8, 1702–1710 (1959). https://doi.org/10.1007/BF00912106

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  • DOI: https://doi.org/10.1007/BF00912106

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