Thionyl Chloride → HCID 86596721, compound

HRID 855971Notes

Reaction equation

[ClH:1].[NH2:2][CH2:3][CH2:4][C@H:5](O)[C:6]([O:8][CH3:9])=[O:7].S(Cl)([Cl:13])=O>>[ClH:13].[NH2:2][CH2:3][CH2:4][C@@H:5]([Cl:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 86596723307316-20-7

Product 1

HCID 86596721HCID 86596721, compound

Procedure

To methyl (S)-4-amino-2-hydroxybutyrate hydrochloride (521.6 mg; 409.5 mg when calculated as methyl (S)-4-amino-2-hydroxybutyrate) was added 1.8 mL of thionyl chloride. The mixture was stirred at room temperature for 3 hours and then at 50 C for 4 hours. Thereafter, the solvent was distilled off under reduced pressure to give 576.2 mg of methyl (R)-4-amino-2-chlorobutyrate hydrochloride (yield quantitative, optical purity 96.9% 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)).

Workup

waitat 50 C for 4 hours
distillationThereafter, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-b02fbe92a1d746fda437711403eb94c1
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262308B2

Reaction notes

Loading…