Hydrogen Peroxide → HCID 67330658, compound

Participants

Reaction Conditions

Reaction Steps

A fresh aqueous solution of LiO2H, prepared from mixing a solution of LiOH (2.1 mL, 3.33 M in water) with H2O2 (1.54 mL, 33% in water) at 0° C., was slowly added to a cooled mixture of 35.3 (2.02 g, 3.39 mmol) in THF (20.0 mL) and water (10 mL) at 0° C. The resulting reaction mixture was stirred at 0° C. for 1.5 hours. The reaction was then quenched by adding a 1.5 N aqueous solution of Na2SO3 at 0° C. Water (150 mL) was added, and the aqueous solution was extracted with diethyl ether (30×3 mL) and acidified with concentrated HCl to a pH of 2. The mixture was then extracted with EtOAc (60×2 mL, 40×2 mL). The organic layer was dried with Na2SO4, and the solvent was removed to give the crude intermediate, (S)-3-(4-(4-chloro-3-(trifluoromethoxy)benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acid. This intermediate was treated with EtOH (20 mL) and HCl (0.5 mL, 1.0 M in ether) at room temperature overnight. The solvent was evaporated to provide the crude product 35.4 which was used without further purification. MS ESI (pos.) m/e: 470 (M+H).

Provenance & Evidence