Hydrochloric Acid → (3R)-3-(3-Isoxazolyl)-3-(3-((phenylmethyl)oxy)phenyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-4-benzyl-3-((R)-3-(3-(benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one (94.1C) (0.558 g, 1.16 mmol) in THF (12 mL) was cooled to 0° C. H2O2 (30% w/w, 0.50 mL) was added, and was followed by addition of LiOH, monohydrate (0.0643 mL, 2.31 mmol) in water (4 mL). The resulting mixture was stirred at 0° C. for 2 hours. The organic solvent was blown away by nitrogen, and the aqueous mixture was acidified with 1N HCl to pH 3-5. The mixture was extracted with EtOAc (100 mL). The organic phase was washed with brine, dried over anhydrous Na2SO4. After removing solvent, crude product (94.1D) (491 mg) was obtained.

Provenance & Evidence