Pyridine → (S)-N-((2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-chloro-5-fluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide

Temperatur

0 °C

To a 50 mL polypropylene bottle containing (S)—N-((2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-(3-chloro-5-fluorophenyl)butan-2-yl)-2-methylpropane-2-sulfinamide (350.00 mg, 618 μmol) was added THF (10 mL ) and the mixture was allowed to stir at 0° C. for 5 minutes. At this time, PYRIDINE (2699 μl, 33371 μmol) was added via syringe before the addition of HF-Pyridine, 70% HF 30% pyr (1782 μl, 19775 μmol) via a syringe. The reaction was allowed to stir at this temp for 2 h and then quenched by pouring into sodium bicarbonate (sat 150 ml). The aq. layer was extracted with EtOAc 94×75 mL). The combined organics were washed with HCl (0.1 N, 3×100 mL), bicarbonate (sat, 100 mL), brine and dried with sodium sulfate. The dried solution was filtered and concentrated to give a yellow oil which was purified on a 40 g ISCO column to give the title compound.

1. stirringto stir at this temp for 2 h
2. customquenched
3. additionby pouring into sodium bicarbonate (sat 150 ml)
4. extractionThe aq. layer was extracted with EtOAc 94×75 mL)
5. washThe combined organics were washed with HCl (0.1 N, 3×100 mL), bicarbonate (sat, 100 mL), brine
6. dry with materialdried with sodium sulfate
7. filtrationThe dried solution was filtered
8. concentrationconcentrated
9. customto give a yellow oil which
10. customwas purified on a 40 g ISCO column

ORD-Eintrag

ord-2133c55f16114c7a9a8c4b048ffd631b

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07745484B2