475288-43-8Relevant academic research and scientific papers
High yielding synthesis of N-ethyl dehydroamino acids
Monteiro, Luís S.,Suárez, Ana S.
, p. 1643 - 1652 (2013/01/14)
Recently we reported the use of Asequence of alkylation and dehydration methodologies to obtain N-ethyl-α, β-dehydroamino acid derivatives. The application of this N-Alkylation procedure to several methyl esters of β,β-dibromo and β-bromo, β-substituted dehydroamino acids protected with standard amine protecting groups was subsequently reported. The corresponding N-ethyl, β-bromo dehydroamino acid derivatives were obtained in fair to high yields and some were used as substrates in Suzuki cross-coupling reactions to give N-ethyl, β,β-disubstituted dehydroalanine derivatives. Herein, we further explore N-ethylation of β-halo dehydroamino acid derivatives using triethyloxonium tetrafluoroborate as alkylating agent, but substituting N,N-diisopropylethylamine for potassium tert-butoxide as auxiliary base. In these conditions, for all β-halo dehydroamino acid derivatives, reactions were complete and the N-ethylated derivative could be isolated in high yield. This method was also applied for N-ethylation of non-halogenated dehydroamino acids. Again, with all compounds the reactions were complete and the N-ethyl dehydroamino acid derivatives could be isolated in high yields. Some of these N-ethyl dehydroamino acid methyl ester derivatives were converted in high yields to their corresponding acids and coupled to an amino acid methyl ester to give N-ethyl dehydrodipeptide derivatives in good yields. Thus, this method constitutes Ageneral procedure for high yielding synthesis of N-ethylated dehydroamino acids, which can be further applied in peptide synthesis.
Synthesis using Suzuki cross couplings of sulfur analogues of dehydrotryptophan with a definite stereochemistry
Silva, Natalia O.,Abreu, Ana S.,Ferreira, Paula M. T.,Monteiro, Luis S.,Queiroz, Maria-Joao R. P.
, p. 2524 - 2528 (2007/10/03)
Sulfur analogues of dehydrotryptophan (5-7) were prepared in moderate to good yields (40-80%) by Suzuki cross coupling [Pd(PPh3)4, Na2CO3 or NaHCO3, DME/H2O, 90°C] of several benzo[b]thioph
