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Synthesis 2008(23): 3739-3741  
DOI: 10.1055/s-0028-1083227
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

tert-Butoxycarbonyl Chloride for the Introduction of N-Boc Groups into Amino Acids

Helmut Vorbrüggen*a,b
a (The Former) Woodward Research Institute, 4000 Basel, Switzerland
b Institut für Chemie und Biochemie, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany
e-Mail: helvor@chemie.fu-berlin.de;
Further Information

Publication History

Received 7 July 2008
Publication Date:
14 November 2008 (online)

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Abstract

tert-Butoxycarbonyl chloride (BocCl) can be generated in situ from tert-butyl alcohol, COCl2, and pyridine at -74 ˚C to introduce the Boc group in high yield into a hindered amino acid. The method is suitable for large-scale preparations of Boc-amino acids.

Key words

Boc chloride - COCl2 - pyridine - mixed anhydrides - amino acids

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