Thionyl Chloride → HCID 86596721, compound

Participants

Reaction Steps

To methyl (S)-4-amino-2-hydroxybutyrate hydrochloride (169.0 mg; 132.7 mg when calculated as methyl (S)-4-amino-2-hydroxybutyrate) was added 3 ml of dioxane, followed by further addition of 178.5 mg of thionyl chloride. The mixture was stirred at room temperature for 2 hours. Thereafter, 2.3 mg of pyridine was added, and the mixture was further stirred at 50° C. for 3 hours. After confirmation of disappearance of the starting material by TLC, the solvent was distilled off under reduced pressure to give 196.8 mg of methyl (R)-4-amino-2-chlorobutyrate hydrochloride (yield quantitative, optical purity 93.9% 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