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Current Chemical Biology

Editor-in-Chief

ISSN (Print): 2212-7968
ISSN (Online): 1872-3136

Synthesis of Dehydrodipeptide and N-ethyl-dehydrodipeptide Derivatives with an α-Aminoisobutyric Acid Residue

Author(s): LuIs S. Monteiro, Silvia M.M.A. Pereira-Lima and Sofia Pereira

Volume 8 , Issue 2 , 2014

Page: [109 - 113] Pages: 5

DOI: 10.2174/2212796809999150204114112

Price: $65

Abstract

Several dipeptides with an N-benzyloxycarbonyl or an N-(tert-butyloxycarbonyl) α-aminoisobutyric acid residue and a β-hydroxyamino acid methyl ester were subjected to dehydration to form dehydrodipeptide derivatives. N-Ethylation of these dipeptides using triethyloxonium tetrafluoroborate with potassium tert-butoxide as auxiliary base led to complex mixtures that failed to render pure products. However, when the 4-nitrophenylsulfonyl protecting group was substituted for the benzyloxycarbonyl or tert-butyloxycarbonyl groups and N,N-diisopropylethylamine was substituted for potassium tert-butoxide, the dehydrodipeptide derivatives were selectively N-alkylated at the amino terminal nitrogen in fair to high yields. Alternatively, N-ethylation can be carried out prior to dehydration. Thus, through a combination of dehydration and N-ethylation procedures, it was possible to obtain dipeptides with α-aminoisobutyric acid and dehydroamino acid residues, which are N-alkylated at the amino terminal nitrogen.

Keywords: Alkylation, dehydration, dehydroamino acids, dehydrodipeptides, α, α-Dialkylglicines, N-Alkyl-dehydrodipeptides, N-Alkylamino acids.

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