tert-Butylsulfinamide, (R)-(+)- → HCID 87126736, compound

To a solution of 3-bromo-isoxazole-5-carbaldehyde (182 mg, 1.03 mmol) and (R)-(+)-2-methyl-2-propanesulfinamide (150 mg, 121 mmol) in CH2Cl2 (2 mL) was added titanium (IV) isopropoxide (0.667 mL, 2.28 mmol) and the mixture was warmed at reflux. After 22 hours, the solvent was concentrated in vacuo and the remaining solution was diluted with EtOAc (33 mL) and saturated aqueous NaCl (6 mL) was added. The resultant heterogeneous mixture was stir at room temperature. After 30 minutes, the 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)-meth-(E)-ylideneamide.

1. temperaturethe mixture was warmed
2. temperatureat reflux
3. concentrationthe solvent was concentrated in vacuo
4. additionthe remaining solution was diluted with EtOAc (33 mL) and saturated aqueous NaCl (6 mL)
5. additionwas added
6. waitAfter 30 minutes
7. filtrationthe mixture was filtered through a pad of diatomaceous earth
8. dry with materialThe EtOAc layer was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude material was purified by silica gel chromatography
12. washeluting with a gradient of 0-100% EtOAc in heptane

ORD record

ord-ad387e8917a849aa969a0a311f71c40a

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063065B2