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-624d3015927d4a4d960b7ce8230a8393

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163918B2