216578-83-5Relevant articles and documents
Synthesis and reactions of α-fluoro-α-amino amides
Bailey, Patrick D.,Boa, Andrew N.,Clayson, Joanne
experimental part, p. 1724 - 1736 (2009/05/09)
N-((S)-1-Phenylethyl)halofluoroethanamides have been investigated as precursors to N-protected α-fluoro-α-amino amides by nucleophilic displacement of halide with nitrogen nucleophiles such as potassium phthalimide, sodium succinimide, sodium glutarimide, trimethylamine and sodium azide. With single diastereoisomers of the iodofluoroethanamide, clean inversion of configuration occurs at room temperature, but subsequent epimerisation may occur as a result of the liberated iodide. The α-fluoro-α-amino amides made underwent a wide variety of reactions depending on conditions, but in many cases the carbon-fluorine bond was compromised. However, reacting trimethylamine and N-((S)-1-phenylethyl)iodofluoroethanamide gave the corresponding α-fluorobetaine amide, and subsequent acidic hydrolysis led to α-fluorobetaine as the first example of an 'unprotected' α-fluoroamino acid.
Synthesis of α-heterosubstituted glycine derivatives from dihaloethanamides
Bailey, Patrick D.,Baker, S. Richard,Boa, Andrew N.,Clayson, Joanne,Rosair, Georgina M.
, p. 7755 - 7758 (2007/10/03)
A range of protected α-heterosubstituted analogues of glycine were synthesised from starting materials of the type CHFX-CONHR [X = Cl, Br, I; R = CH2Ph, (s)-CHMePh]; the final products included derivatives of glycine possessing N, O, F or S in the α-position, and the first example of a free α-fluoro-α-amino acid (α-fluorobetaine) whose structure was confirmed by X-ray crystal structure determination.
