m-Chloroperbenzoic acid → HCID 58109705, compound

Participants

Reaction Steps

To a solution of (R)-6-allyl-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (900 mg, 2.0 mmol) in dry CH2Cl2 (30 mL) was added dropwise 3-chlorobenzoperoxoic acid (690 mg, 4.0 mmol) by portion at 0° C. Then the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was quenched by 10% Na2SO3 solution. The organic phase was dried over Na2SO4, filtered and concentrated to afford the residue, which was purified by TLC to give (6S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(oxiran-2-ylmethyl)-1,3-oxazinan-2-one (470 mg, 50%). 1H NMR (CDCl3): 1.54 (m, 3H), 1.71 (m, 3H), 2.01 (m, 1H), 2.15 (m, 3H), 2.48 (m, 2H), 2.67 (m, 1H), 3.00 (m, 1H), 5.67 (m, 1H), 6.84 (m, 4H), 7.02 (m, 2H), 7.21 (m, 4H), 7.31 (m, 1H).

Provenance & Evidence