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Synlett 2011(14): 2013-2016  
DOI: 10.1055/s-0030-1261160
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Tarek S. Ibrahima,b, Srinivasa R. Talaa,, Said A. El-Fekyb, Zakaria K. Abdel-Samiib, Alan R. Katritzky*a,c
a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;
b Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Zagazige University, Zagazig 44519, Egypt
c Chemistry Department, King Abdulaziz University, Jeddah 21589, Saudi Arabia
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Publication History

Received 29 April 2011
Publication Date:
10 August 2011 (online)

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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 as reagents to introduce α-amino protecting groups to afford Fmoc-, Boc-, and Alloc-protected amino acids (77-94%) free of dipeptide and tripeptide impurities. Fmoc-, and Alloc-Gly-Gly-OH dipeptides were prepared in 90% yields by N-acylation of glycylglycine with Fmoc- and Alloc-benzotriazoles in the presence of triethylamine. Synthesized N-protected amino acids were greater than 99% pure, analyzed by HPLC.

Key words

amino acids - benzotriazole - protecting groups - acylation - HPLC

1

Present address: Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis, MN 55455, USA.