Sodium Chloride → Butanoic acid, 2-hydroxy-4-(methylthio)-, methyl ester

A solution of DL, 2-hydroxy-4-methylmercaptobutyric acid calcium salt (2.2 g) in 0.5M HCl (50 mL) was saturated with sodium chloride, extracted exhaustively with EtOAc, which was dried (MgSO4), filtered and concentrated. The residue was dissolved in methanol (10 mL) and trimethylsilyldiazomethane (2M in hexane) was added until the yellow color persisted for 30 min. The reaction was quenched by addition of glacial acetic acid and concentrated. The residue was purified by silica gel chromatography eluting with 30% EtOAc/hexane to give the title compound as a light yellow oil (1.37 g).

1. extractionextracted exhaustively with EtOAc, which
2. dry with materialwas dried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in methanol (10 mL)
6. additiontrimethylsilyldiazomethane (2M in hexane) was added until the yellow color
7. customThe reaction was quenched by addition of glacial acetic acid
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography
10. washeluting with 30% EtOAc/hexane

ORD record

ord-c2e853c040ce4e7d820cb21bd31b4f83

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310095B1