Synthesis 1990; 1990(7): 571-572
DOI: 10.1055/s-1990-26943
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A Simple and Convenient Synthesis of ω-tert-Butyl Esters of Fmoc-Aspartic and Fmoc-Glutamic Acids

Gilles Lajoie* , Anna Crivici, J. Gordon Adamson
  • *Department of Chemistry, University of Waterloo, Canada N2L 3G1
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17. September 2002 (online)

N-(9-Fluorenylmethoxycarbonyl)aspartic acid β-tert-butyl ester (3b) [Fmoc-Asp(OBu-t)] and N-(9-fluorenylmethoxycarbonyl)-glutamic acid γ-tert -butyl ester (4b) [Fmoc-Glu(OBu-t)] were prepared from aspartic and glutamic acids by treatment with isobutene and 4-toluenesulfonic acid followed by Fmocsuccinimide in a novel two-step, one-pot procedure to give the title compounds in moderate yield. The major byproduct of the reaction is the corresponding α-tert-butyl ester, which can be easily separated and purified.