84677-05-4Relevant articles and documents
The synthesis of α,α-disubstituted α-amino acids via ichikawa rearrangement
Szczes?niak, Piotr,Pieczykolan, Micha?,Stecko, Sebastian
, p. 1057 - 1074 (2016/02/19)
An approach to α,α-disubstituted α-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X7-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.
1-Aminocylopropane-1-carboxylic acid derivatives as ligands at the glycine-binding site of the N-methyl-D-aspartate receptor
Balsamini, Cesarino,Bedini, Annalida,Spadoni, Gilberto,Tarzia, Giorgio,Tontini, Andrea,Balduini, Walter,Cimino, Mauro
, p. 181 - 188 (2007/10/03)
Several 1-aminocyclopropane-1-carboxylic acid derivatives were prepared and tested for activity at the glycine-binding site of the N-methyl-D- aspartate (NMDA) receptor complex. Structural modifications involved the amino group, the carboxylic function or
A Simple Synthesis of 1-Aminocyclopropane-1-carboxylic Acid
Strazewski, Peter,Tamm, Christoph
, p. 298 - 299 (2007/10/02)
Conversion of N-carbobenzyloxy-L-glutamic acid α-methylester (Z-L-glu(OH)OCH3, 1) into the bromo derivative 2 and subsequent γ-elimination by the use of sodium hydride leads to the fully protected synthon 3 in good yields.Deprotection by sodium hydroxide and hydrogenolysis yields almost quantitively the key substance 5.