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Azide Formation

By: Matthias Junkers, Aldrich ChemFiles 2007, 7.2, 3.

Azide coupling procedures were introduced by Curtius as one of the first successful strategies for the synthesis of peptides. For a long time they were thought to be the only racemisation free method. A very convenient way to form N-acylamino acid azides is to apply DPPA (diphenyl phosphoryl azide). This method is particularly useful in cyclization reactions of peptides.1,2 DPPA can also be used in the preparation of urethanes by reaction with alcohols.

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  1. Hoffmann, E.; Beck-Sickinger, A. G.; Jung, G. Liebigs Ann. Chem 1991, 585.
  2. Yamada, T.; Omote, Y.; Nakamura, Y.; Miyazawa, T.; Kuwata, S. Chem. Lett. 1993, 1583.

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