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 |
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Authors: | Till?R?hrich Bassam Abu?Thaher Email author" target="_blank">Hans-Hartwig?OttoEmail author |
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Institution: | (1) Department of Pharmaceutical/Medicinal Chemistry (PMC), Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, DE-17487 Greifswald, Germany, DE |
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Abstract: | 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 -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. |
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Keywords: | -Sultam, -Sultam peptide," target="_blank">, 1,2-Thiazetidine 1,1-dioxide, -Sultam, -Sultam peptide, |
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