273. N-substituted amino-acids. Part II. The reductive alkylation of amino-acids

Synthesis of N‐Alkyl Amino Acids

“…In a series of papers, Bowman et al [52][53][54] describe the N,N-dimethylation of amino acids with formalin over palladium-on-charcoal catalyst under hydrogenolytic conditions. The work in this paper was concerned with dimethylation, and provided quantitative yields of the N,N-dimethyl amino acids of alanine, valine, leucine, phenylalanine, tyrosine, cysteine, aspartic acid, and glutamic acid.…”

“…The second paper [53] extends the methodology to the mono N-alkylation of valine, leucine, and phenylglycine with various aldehydes in ethanol or aqueous ethanol. In this case N,N-dialkylglycine can also be produced, whereas amino acids other than glycine were only mono-N-alkylated [53].…”

“…In this case N,N-dialkylglycine can also be produced, whereas amino acids other than glycine were only mono-N-alkylated [53]. The last paper [54] describes the reductive alkylation of peptides for identifying the N-terminal amino acid in the chain, employing the same protocols as the two previous papers [54].…”

“…Reductive amination involving transition metal hydrogenolysis is somewhat limited to dimethylation with formaldehyde, but monoalkylation with aldehydes other than formaldehyde is possible [52][53][54].…”

Enantiomeric Separation of Underivatized Aliphatic β-Amino Alcohols by Ligand-exchange Chromatography usingN-n-Dodecyl-(1R,2S)-norephedrine as a Coating Reagent for Reversed-phase Column

“…C 12 -NE was prepared according to the modified procedure of Bowman [5]: 0.02 mol (3.02 g) of NE and 0.02 mol (3.69 g) of dodecyl aldehyde were dissolved in 100 ml of ethanol. One gram of 5% palladium on activated charcoal catalyst was added to the solution as a suspension.…”