Tetrabutylammonium Fluoride → HCID 67060891, compound

To a solution of (4S)-4-(tert-butyl)-3-(phenylmethyl)-1,2,3-oxathiazolidine-2,2-dioxide (6.22 g, 23.09 mmol) in THF (100 mL) was added a 1 M solution of tetrabutylammonium fluoride in THF (46.2 ml, 46.2 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. Solvent was evaporated, and ether (50 mL) and 20% H2SO4 aqueous solution (20 mL) were added. The reaction mixture was stirred for 2 h at room temperature, diluted with water, neutralized with solid NaHCO3 slowly then extracted with ethyl acetate. The combined organics were dried over anhydrous Na2SO4, filtered, then concentrated. The residue was purified by column chromatography to give the title compound (4.13 g) as a light yellow oil. LCMS m/z=210.4 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 0.96 (s, 9H), 2.41 (dt, J=24.7 and 4.3 Hz, 1H), 3.76 (d, J=13.1 Hz, 1H), 4.01 (d, J=13.1 Hz, 1H), 4.39-4.72 (m, 2H), 7.23-7.38 (m, 5H).

1. customSolvent was evaporated
2. additionether (50 mL) and 20% H2SO4 aqueous solution (20 mL) were added
3. stirringThe reaction mixture was stirred for 2 h at room temperature
4. additiondiluted with water
5. extractionextracted with ethyl acetate
6. dry with materialThe combined organics were dried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by column chromatography

ORD record

ord-6e91e23a7a8f451696b3499c211760da

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778950B2