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Benzotriazole Reagents for the Syntheses of Fmoc-, Boc-, and Alloc-Protected Amino Acids

Tarek S. Ibrahima, Srinivasa R. Tala, Said A. El-Feky, Zakaria K. Abdel-Samii, Alan R. Katritzky*

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA, Email: katritzkychem.ufl.edu

T. S. Ibrahima, S. R. Tala, S. A. El-Feky, Z. K. Abdel-Samii, A. R. Katritzky, Synlett, 2011, 2013-2016.

DOI: 10.1055/s-0030-1261160 (free Supporting Information)



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Abstract

Stable Fmoc-, Boc-, and Alloc-benzotriazoles react with various amino acids including unprotected serine and glutamic acid, in the presence of triethylamine at 20˚C to afford Fmoc-, Boc-, and Alloc-protected amino acids in very good yields free of dipeptide and tripeptide impurities. Fmoc-, and Alloc-Gly-Gly-OH dipeptides were prepared in excellent yields by N-acylation of glycylglycine.

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Key Words

amino acids, benzotriazole, protecting groups (FMOC, BOC), acylation, carbamates


ID: J60-Y2011-2410