494868-30-3

Upstream product

• 3481-15-0 (S)-[α-D]-benzyl alcohol 
• 124-63-0 methanesulfonyl chloride 
• 100-52-7 benzaldehyde 
• 15190-10-0 morpholin-4-yl-phenyl-acetonitrile 
• 3592-47-0 Benzaldehyde-d 
• 26593-35-1 α-phenyl-4-morpholineacetonitrile-α-d 

Relevant academic research and scientific papers

Stereoselective route to 15N-labeled-β-deuterated amino acids: Synthesis of (2S,3R)-[3-2H,15N]-phenylalanine

(2S,3R)-[3-2H,15N]-Phenylalanine hydrochloride was synthesized utilizing 15N-labeled 8-phenylmenthylhippurate as a chiral glycine equivalent. The key step in the synthesis was the alkylation of the glycine template with (S)-(+)-benzyl-α-d-mesylate. The doubly labeled alkylation product was obtained in 89% yield with 92% de at the α-carbon and 74% de at the β-carbon. The nature of the electrophile employed in the alkylation step significantly affects the stereochemical outcome at the β-carbon. Hydrolysis of the alkylation product under acidic conditions followed by recrystallization from isopropanol yielded the title compound as the hydrochloride salt. Analysis of the (-)-camphanamide derivative of the final product by NMR spectroscopy and HPLC revealed a 76% de at the α-carbon and a 72% de at the β-carbon. The synthetic strategy described represents a simple yet versatile route to chirally deuterated β-methylene unit containing amino acids.