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1H NMR analysis is complicated by the presence of amide rotamers. The involatility of 1 made capillary GC analysis impractical, and conditions for the separation of the diastereomeric alkylation products by HPLC have not been found.
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In order to properly identify the minor enantiomer for HPLC analysis, D-azatyrosine was prepared by alkylation of the enantiomeric pseudoephedrine glycinamide ((S,S)-(+)-2) with iodide 6 followed by alkaline hydrolysis. D-Azatyrosine showed equivalent spectroscopic properties as L-azatyrosine, but opposite optical rotation.
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note
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In contrast to other alkyl halides we have studied, small amounts of N-alkylation products are observed (<5%) during the alkylation with the highly reactive electrophile 6 whenever the reactions are conducted above -78 °C. These N-alkylation products are readily separated from the desired product by chromatography.
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