Thionyl Chloride → HCID 86596721, compound

Participants

Reaction Conditions

Reaction Steps

To methyl (S)-4-amino-2-hydroxybutyrate hydrochloride (498 mg; 391 mg when calculated as methyl (S)-4-amino-2-hydroxybutyrate) was added 5 ml of 4 N-HCl/dioxane, followed by further addition of 321 μL of thionyl chloride. The mixture was stirred at 50° C. for 4 hours. The solvent was distilled off under reduced pressure to give 530 mg of methyl (R)-4-amino-2-chlorobutyrate hydrochloride (yield quantitative, optical purity 98.5% ee). The analysis of the optical purity was carried out by derivatizing into (R)-3-chloro-2-pyrrolidinone with sodium hydrogen carbonate, followed by high performance liquid chromatography using a chiral column (Chiralcel OB-H (Daicel)).

Provenance & Evidence