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Synthesis 1992; 1992(11): 1093-1095
DOI: 10.1055/s-1992-26312
short paper
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The Use of Polymer-Bound Triphenylphosphine and Carbon Tetrachloride for Condensation of N-Alkoxycarbonyl α-Amino Acids and Primary Amines

John J. Landi, Jr.* , Herbert R. Brinkman
  • *Synthesis Development, Hoffmann-La Roche Inc., Nutley, New Jersey 07110, USA
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Publication Date:
17 September 2002 (online)

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The combination of carbon tetrachloride and polymer-bound tri-phenylphosphine is shown to be useful for coupling N-alkoxycarbonyl α-amino acids and primary amines including amino acid esters. The three major N-protecting groups, CBz, Boc, and FMOC are well tolerated. The product amides are isolated in 78-100% yields with negligible epimerization of the α-carbon.

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