Ceric ammonium nitrate → HCID 58109448, compound

Participants

Reaction Steps

To a solution of methyl (R)-3-((S)-1-(4-(2-hydroxy-2-methylpropyl)phenyl)ethyl)-6-(3-(4-methoxybenzyloxy)propyl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 0.188 mmol) in DCM/H2O (10:1, 2 mL) was added CAN (100 mg). The formed mixture was stirred for 3 h. The reaction was washed with water and extracted with CH2Cl2. The combined organic phase was concentrated to provide the crude product, which was purified by preparative HPLC to give (R)-3-((S)-1-(4-(2-hydroxy-2-methylpropyl)phenyl)ethyl)-6-(3-(4-methoxybenzyloxy)propyl)-6-phenyl-1,3-oxazinan-2-one (0.8 mg, 10%). LC-MS Method 2 tR=1.191 min, m/z=411.24; 1H NMR (CDCl3): δ=0.81 (m, 4H), 1.09 (d, 6H), 1.43 (d, 3H), 1.64 (m, 3H), 1.92 (m, 3H), 2.16-2.26 (m, 4H), 2.59 (s, 2H), 2.83 (m, 1H), 3.52 (t, 2H), 5.62 (q, 1H), 6.78 (m, 2H), 6.86 (m, 2H), 6.94 (m, 1H), 7.26 (m, 4H).

Provenance & Evidence