Ozone → HCID 58109636, compound

Participants

Reaction Steps

A solution of (S)-6-(2-(allyloxy)ethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (100 mg, 0.20 mmol) in CH2Cl2 (10 mL) was treated with O3 at −78° C. till the mixture was turned blue. Then NaBH4 (50 mg, 1.0 mmol) was added, and the mixture was stirred at rt overnight. The solution was concentrated and the residue was purified by preparative HPLC to give (S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-(2-hydroxyethoxy)ethyl)-1,3-oxazinan-2-one (40 mg, 30%). LC-MS Method 3 tR=1.41, min, m/z=500, 522; 1H NMR (CDCl3): 1.48-1.61 (d, 3H), 1.92-2.05 (m, 2H), 2.09-2.41 (m, 5H), 2.88-3.02 (m, 1H), 3.27-3.56 (m, 2H), 3.58-3.69 (m, 2H), 5.63-5.72 (m, 1H), 6.82-7.08 (m, 6H), 7.17-7.34 (m, 5H).

Provenance & Evidence