Synthesis of N-methylpyrrole and N-methylimidazole amino acids suitable for solid-phase synthesis.
New and higher yielding synthetic routes to N-protected N-methylpyrrole and N-methylimidazole amino acids are introduced to circumvent difficulties associated with established schemes. Key steps in each synthesis include copper-mediated cross-coupling reaction to directly install a carbamate-protected 4-amine in the N-methylpyrrole derivative and effective nitration followed by a one-pot reduction/Boc protection of the amine in the synthesis of the N-Me-imidazole amino acid.
Jaramillo
David
D
College of Science, Technology & Environment, University of Western Sydney, Penrith South DC NSW 2560, Australia.
Liu
Qi
Q
Aldrich-Wright
Janice
J
Tor
Yitzhak
Y
D000596:Amino Acids / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D007093:Imidazoles; D011758:Pyrroles