Activation of carboxylic acids by pyrocarbonates. Synthesis of arylamides of N ‐protected amino acids and small peptides using dialkyl pyrocarbonates as condensing reagents
- 1 July 1994
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 44 (1) , 36-48
- https://doi.org/10.1111/j.1399-3011.1994.tb00402.x
Abstract
Activation of carboxylic acids was achieved via dialkyl pyrocarbonates (ROCO)2O, (R = ethyl, isopropyl, sec‐butyl, tert‐butyl) in aprotic solvents in the presence of tertiary amines. A convenient one‐pot procedure for the preparation of arylamides from N‐protected amino acids including arginine and from di‐tert‐butyl pyrocarbonate in the presence of pyridine (Boc2O‐pyridine system) was reported. Analogously, diisopropyl, di‐sec‐butyl or diethyl pyrocarbonate could be used in the presence of N‐methylmorpholine or triethylamine. A wide variety of N‐protected amino acid arylamides were prepared in good yields.Keywords
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