90600-00-3Relevant academic research and scientific papers
Electrophilic Amination of Amino Acids with N-Boc-oxaziridines: Efficient Preparation of N-Orthogonally Diprotected Hydrazino Acids and Piperazic Acid Derivatives
Hannachi, Jean-Christophe,Vidal, Joelle,Mulatier, Jean-Christophe,Collet, Andre
, p. 2367 - 2373 (2007/10/03)
A general two-step preparation of enantiopure Nα,N β-orthogonally diprotected α-hydrazino acids 1 is developed on a multigram scale. The key reaction is the efficient electrophilic amination of N-benzyl amino acids 6 with N-Boc-oxaziridine 7 and accommodates various functional groups encountered in side chains of amino acids. The cyclic 2,3,4,5-tetrahydro-3-pyridazine carboxylic acid (piperazic acid) derivatives 2 and 3 or the cyclic 3,4-dihydro-3-pyrazolecarboxylate 4 are conveniently prepared from glutamic acid or aspartic acid via orthogonally diprotected α-hydrazino acids 1m and 1n.
AN EFFICIENT ONE-STEP REDUCTIVE N-MONOALKYLATION OF α-AMINO ACIDS
Ohfune, Yasufumi,Kurokawa, Natsuko,Higuchi, Naoki,Saito, Masayuki,Hashimoto, Masaki,et al.
, p. 441 - 444 (2007/10/02)
Reactions of protection-free α-amino acids with aldehydes or ketones in the presence of sodium cyanoborohydride afforded the N-monoalkylated amino acids in inorganic salt-free form.Application of this method to synthesis of N-alkyl derivatives of biologic
