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Monatshefte für Chemie / Chemical Monthly

, Volume 135, Issue 1, pp 55–68 | Cite as

Substituted 1,2-Thiazetidine 1,1-Dioxides. Synthesis and Properties of N-Alkylated and N-Acylated Derivatives of 1,2-Thiazetidine-3-acetic Acid 1,1-Dioxide

  • Till Röhrich
  • Bassam Abu Thaher
  • Hans-Hartwig OttoEmail author

Summary.

1,2-Thiazetidine-3-acetic acid 1,1-dioxide was N-alkylated using bromoacetates, and N-acylated using either acyl chlorides, protected amino acid fluorides, or N-protected amino acid NCA, which seemed to be the most universal method. Most of the obtained “β-sultam peptides” were sensitive against humidity, they hydrolyzed forming sulfonic acids, and reactions with amines resulted in sulfonamides. Reactions of N-acylated products showed that the sulfonyl group was faster attacked than the imide structure.

Keywords. 1,2-Thiazetidine 1,1-dioxide; β-Sultam; β-Sultam peptide. 

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Copyright information

© Springer-Verlag/Wien 2003

Authors and Affiliations

  • Till Röhrich
    • 1
  • Bassam Abu Thaher
    • 1
  • Hans-Hartwig Otto
    • 1
    Email author
  1. 1.Department of Pharmaceutical/Medicinal Chemistry (PMC), Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, DE-17487 Greifswald, GermanyDE

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