tert-Butylsulfinamide, (R)-(+)- → (NE)-N-[1-(3-bromo-1,2-oxazol-5-yl)propylidene]-2-methylpropane-2-sulfinamide

Temperature

45 °C

To a solution of 1-(3-bromo-isoxazol-5-yl)-propan-1-one (452 mg, 2.22 mmol) and (R)-(+)-2-methyl-2-propanesulfinamide (342 mg, 2.82 mmol) in CH2Cl2 (5 mL) was added titanium (IV) isopropoxide (1.4 mL, 4.9 mmol) and the mixture was warmed at 45° C. After 24 hours, the reaction was monitored by LC-MS, and the solvent was concentrated in vacuo and the remaining residue was diluted with EtOAc (32 mL) and saturated aqueous NaCl (8 mL) was added. The heterogeneous mixture was filtered through a pad of diatomaceous earth. The EtOAc layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in heptane to afford 2-methyl-propane-2-sulfinic acid [1-(3-bromo-isoxazol-5-yl)-prop-(E)-ylidene]-amide. MS m/z 307 (M), 309 (M+2).

1. concentrationthe solvent was concentrated in vacuo
2. additionthe remaining residue was diluted with EtOAc (32 mL) and saturated aqueous NaCl (8 mL)
3. additionwas added
4. filtrationThe heterogeneous mixture was filtered through a pad of diatomaceous earth
5. dry with materialThe EtOAc layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude material was purified by silica gel chromatography
9. washeluting with a gradient of 0-100% EtOAc in heptane

ORD record

ord-ef69969295554abd838feedff6dca926

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879873B2