A novel and practical synthesis of (R)-serine-2-d that is stoichiometric in its use of deuterium is described. Isopropyl (R,S)-2-phenyl-2-oxazoline-4-carboxylate is metalated, deuteriated, resolved, and hydrolyzed to provide the optically pure (>99.8%) unnatural amino acid with >98% isotopic purity. Fluorination of the primary hydroxyl with SF4 produces (S)-3-fluoroalanine-2-d (Fludalanine).
|Original language||English (US)|
|Number of pages||9|
|Journal||Journal of Organic Chemistry|
|State||Published - Jul 1 1987|
All Science Journal Classification (ASJC) codes
- Organic Chemistry