PDF herunterladen
Synthesis 1994; 1994(5): 480-482
DOI: 10.1055/s-1994-25507
short paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

An Efficient Synthesis of Aryl Phenaceturates Using Acid Catalyzed Dicyclohexylcarbodiimide Esterification and Transient N-trent-Butoxycarbonylation

Daniel Cabaret* , Jie Liu, Michel Wakselman
  • *CNRS-CERCOA, 2 rue Henri Dunant, F-94320 Thiais, France
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
17. September 2002 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Application of the Holmberg procedure (DCC/pyridine/p-TSAcat) improves the yield of the direct condensation of phenols with phenylacetylglycine (1). Moreover, N-tert-butoxycarbonylation of 1 impedes an intramolecular reaction leading to an oxazolone, and allows the formation of stable aryl N-Boc phenaceturates. Then, mild cleavage of the Boc group with four equivalents of trifluoroacetic acid furnishes the aryl phenylacetylglycinate. This indirect method is more efficient than its direct analog in the case of phenols possessing electron-withdrawing substituents.