Triacetoxyperiodinane → HCID 86732234, compound

To a solution of (R)-N-((S)-2-(2,3-difluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide (14.56 g, 47.7 mmol) in DCM (250 ml) at room temperature was added Dess-Martin periodinane (22.24 g, 52.4 mmol) in one portion. The reaction was stirred at room temperature overnight. The reaction was quenched with water (150 ml) and saturated NaHCO3 solution (150 ml). The resulted solution was diluted with DCM and the layers were separated. The organic layer was washed with saturated NaHCO3 (3×), water and brine. The solution was then dried over Na2SO4 and filtered. The filtrate was concentrated and purified by silica gel column (20-65% EtOAc/hexane) to afford (R)-N-((S)-2-(2,3-difluorophenyl)-4-oxobutan-2-yl)-2-methylpropane-2-sulfinamide (13.5 g, 44.5 mmol, 93% yield) as light yellow oil. MS m/z=304.1 [M+H]+. Calculated for C14H19F2NO2S: 303.4

1. customThe reaction was quenched with water (150 ml) and saturated NaHCO3 solution (150 ml)
2. additionThe resulted solution was diluted with DCM
3. customthe layers were separated
4. washThe organic layer was washed with saturated NaHCO3 (3×), water and brine
5. dry with materialThe solution was then dried over Na2SO4
6. filtrationfiltered
7. concentrationThe filtrate was concentrated
8. custompurified by silica gel column (20-65% EtOAc/hexane)

ORD record

ord-d4e39474f6a045feac41015c1128c3a3

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296734B2