Carbon Disulfide → (4S)-3,4-Bis(2-methylpropyl)-2-thiazolidinethione

To a mixture of (2S)4-methyl-2-(isobutylamino)pentan-1-ol HCl salt (Method B4c; 0.21 g, 1.0 mmol) and CS2 (0.30 mL, 5.0 mmol, 5.0 equiv.) in 2-butanone (20 mL) was added Cs2CO3 (0.72 g, 2.20 mmol, 2.2 equiv.) and the resulting mixture was heated at the reflux temp. overnight. The resulting orange solution was concentrated under reduced pressure and the residue was triturated with EtOAc (25 mL). The remaining solids were washed with EtOAc (25 mL), and the combined EtOAc phases were concentrated under reduced pressure. The residue was absorbed onto SiO2 and purified by MPLC (Biotage 40 S silica gel column; 5% EtOAc/hex) to give (4S)-3,4diisobutyl 1,3-thiazolidin-2-thione as a yellow oil (0.11 g, 52%).

1. temperaturethe resulting mixture was heated at the reflux temp
2. customovernight
3. concentrationThe resulting orange solution was concentrated under reduced pressure
4. customthe residue was triturated with EtOAc (25 mL)
5. washThe remaining solids were washed with EtOAc (25 mL)
6. concentrationthe combined EtOAc phases were concentrated under reduced pressure
7. customThe residue was absorbed onto SiO2
8. custompurified by MPLC (Biotage 40 S silica gel column; 5% EtOAc/hex)

ORD record

ord-ad41081e9c124d19afa1a109119e4d25

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06353006B1