Abstract
Foundation for Science and Technology (FCT) – Portugal and Fundo Europeu de Desenvolvimento Regional (FEDER) for financial support to Chemistry Centre of University of Minho. The NMR spectrometer Bruker Avance II+ 400 is part of the National NMR Network and was purchased in the framework of the National Program for Scientific Re-equipment; contract REDE/1517/RMN/2005, with funds from POCI 2010, FEDER and FCT.
Highlights
Non-proteinogenic amino acids are an important class of organic compounds with a large application spectrum in medicinal chemistry, since they can have intrinsic biological activity or can be found in peptides with antibiotic, antiviral, antitumor, anti-inflammatory or immunosuppressive activities
A trialkyloxonium tetrafluoroborate / potassium tert-butoxide alkylation procedure was applied for N-alkylation of several methyl esters of Cα,α-dimethylglycines, N-protected with several types of amine protecting groups
All N-alkyl, Cα,α-dimethylglycine derivatives could be obtained in high yields
Summary
Non-proteinogenic amino acids are an important class of organic compounds with a large application spectrum in medicinal chemistry, since they can have intrinsic biological activity or can be found in peptides with antibiotic, antiviral, antitumor, anti-inflammatory or immunosuppressive activities. The same procedure but using trimethyloxonium tetrafluoroborate as alkylating agent is described to give N-methylated derivatives of Cα,α-dimethylglycine. Other Cα,α-dimethylglycine methyl ester derivatives with different types of amine protecting groups, namely, the benzyloxycarbonyl (Z), the 4nitrobenzenesulfonyl (Nosyl), the 4-toluenesulfonyl (Tos), the benzoyl (Bz) and the acetyl (Ac) group were prepared (compounds 1b-f, Scheme 1) and subject to N-ethylation in the same conditions.
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