Reaktion #686313

Reaktionsgleichung

Na2SO3

4-benzyl-3-{2-[5-(4-fluoro-2-trifluoromethyl-benzyloxy)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoyl}-oxazolidin-2-one

LiOH.H2O

H2O2

→

(R)-2-[5-(4-Fluoro-2-trifluoromethyl-benzyloxy)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid

Ausbeute 75.2%

Lösungsmittel

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe excess H2O2 was quenched
2. 2
   workup.STIRRINGstirred at room temperature for 5 min
3. 3
   SonstigeThe organic solvent was removed in vacuo
4. 4
   workup.ADDITIONby adding 1 N aqueous HCl solution
5. 5
   ExtraktionThe aqueous layer was extracted with EtOAc (3×50 mL)
6. 6
   Trocknendried (MgSO4)
7. 7
   EinengenThe mixture was concentrated in vacuo
8. 8
   Sonstigewas purified by ISCO silica gel column chromatography

Vorschrift

To a solution of 4-benzyl-3-{2-[5-(4-fluoro-2-trifluoromethyl-benzyloxy)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoyl}-oxazolidin-2-one (0.535 g, 0.78 mmol) in THF (9 mL) was added water (3 mL). The system was cooled to 0° C. To this cold solution was added LiOH.H2O (33 mg, 0.78 mmol) and 30% H2O2 (0.354 mL, 3.12 mmol,) and stirred at 0° C. for 20 min. The excess H2O2 was quenched by adding 1.5 M aqueous Na2SO3 solution (2.08 mL, 3.12 mmol) and stirred at room temperature for 5 min. The organic solvent was removed in vacuo. The resulting liquid was acidified to pH 2 by adding 1 N aqueous HCl solution. The aqueous layer was extracted with EtOAc (3×50 mL) and dried (MgSO4). The mixture was concentrated in vacuo to receive a crude mixture which was purified by ISCO silica gel column chromatography to yield (R)-2-[5-(4-Fluoro-2-trifluoromethyl-benzyloxy)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid (310 mg).

Quelle