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Simple and efficient preparation of (R)- and (S)-enantiomers of alpha-carbon deuterium-labelled alpha-amino acids
A procedure for the synthesis of (R)- and (S)-enantiomers of alpha-carbon deuterium-labelled alpha-amino acids, exemplified for (R)- and (S)-[2-2H1]-Leu is described. Starting from the respective (S)- or (R)-enantiomer or from the racemic mixture of an alpha-amino acid the selective proton exchange at the alpha-carbon is carried out by racemization via a Schiff base in monodeuterated acetic acid as solvent which serves as deuterium source. After N-protection the racemic mixture is liquid chromatographically separated into the individual (R)- and (S)-enantiomers on preparative scale employing a chiral anion exchanger based on carbamoylated quinine as chiral selector. After deprotection the enantiomerically pure products can be obtained in good yields.
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Reference：
Pyridazine – Wikipedia,
Pyridazine | C4H4N2699 – PubChem