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

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-Eintrag

ord-0279b0d5a958453195ccac72e8ef66b3

Quelldatensatz

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08163918B2