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Synthesis 1995; 1995(2): 168-170
DOI: 10.1055/s-1995-3868
short paper
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Diethoxymethyl: A Useful Nitrogen-Protecting Group for Lactams and Amides

Peter Gmeiner* , Bernd Bollinger
  • *Pharmazeutisches Institut der Universität Bonn, An der Immenburg 4, 53121 Bonn, Germany
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Publication Date:
31 December 2000 (online)

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Treatment of the lactams 3a-e and the amide 3f with triethyl orthoformate leads to the N-diethoxymethyl substituted derivatives 4a-f. Additionally, the indolinones 3a and 3b can react at the lactam α-position to give the reaction products 2 and 5, respectively. The diethoxymethyl group can be easily removed by subsequent treatment with trifluoroacetic acid and NaOH.

Protection of lactams and amides by diethoxymethyl is described.