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Synthesis 1987; 1987(4): 418-420
DOI: 10.1055/s-1987-27971
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A New Synthesis of N-Hydroxyamides Using Trimethylsilyl Protection

Łucja Nakonieczna* , Andrzej Chimiak
  • *Department of Organic Chemistry, Technical University of Gdańsk, PL-80-952 Gdańsk, Poland
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Publikationsdatum:
20. August 2002 (online)

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The concept of transient hydroxylamine oxygen protection for the unambiguous synthesis of N-hydroxyamides has been applied in the amino acid field. First, hydroxylamines 1 were silylated in pyridine with chlorotrimethylsilane; then 2 was immediately N-acylated with mixed anhydride 3 of a protected amino acid or peptide; and finally, the O-trimethylsilyl protection was removed during the isolation procedure giving pure N-hydroxyamides 5.

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