Water → HCID 58109484, compound

Participants

Reaction Steps

CrO3 (1 g) was added to H2SO4 (1 mL) and water was added to bring the total volume to 4 mL. (R)-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (600 mg, 1.4 mmol) was dissolved in 10 mL acetone, and cooled in an ice bath. The Jones reagent (0.5 mL) was slowly added to the mixture and stirred overnight. Solvent was removed in vacuo, the residue was dissolved in CH2Cl2 (10 mL) and water (10 mL). The layers were separated, and the aq layer was extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give 3-((R)-3-((S)-1-(4′-fluorobiphenyl-4-yl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)propanoic acid (500 mg, crude), which was not purified.

Provenance & Evidence