21196-74-7Relevant academic research and scientific papers
Reaction of N-Benzoyl-2-bromoglycine Methyl Ester with Deprotonated Nitroalkanes: Synthesis of β-Nitro and α,β-Dehydro Amino Acid Derivatives
Burgess, Vicky A.,Easton, Christopher J.
, p. 1063 - 1070 (2007/10/02)
N-Benzoyl-2-bromoglycine methyl ester (1) reacted with the alkyl nitronates (2a-e) to give the corresponding β-nitro amino acid derivatives (4a-e).Elimination reactions of (4a-d) afforded the α,β-dehydro amino acid derivatives (5a-d).Treatment of the β-nitrovaline derivative (4b) with tributyltin hydride gave the valine derivative (8).Reduction of the β-nitroalanine derivative (4a) gave the β-aminoalanine derivative (9), characterized by hydrolysis to 2,3-diaminopropionic acid hydrochloride
Dimerization of Glycine Derivatives
Burgess, Vicky A.,Easton, Christopher J.,Hay, Michael P.,Steel, Peter J.
, p. 701 - 710 (2007/10/02)
The bromide (5), prepared by treatment of the glycine derivative (4) with N-bromosuccinimide, reacted with hexabutylditin to give diastereoisomers of the glycine dimer (7), only when moisture was rigorously excluded from the reaction.Otherwise the major products were the diastereoisomers of the ether (11).The structure of the racemic diastereoisomer (11) was determined by X-ray crystallography.Photolysis of mixtures of the glycine derivative (4) and di-t-butyl peroxide gave the alanine derivative (10) in addition to the diastereoisomeric dimers (7).
