HCID 25152049, compound → HCID 68409918, compound

Participants

Reaction Steps

To a solution of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[3-(4-methoxybenzyl)-5-methyl-2-oxo-1,3-oxazolidin-5-yl]methyl}benzamide (598 mg, EXAMPLE 65) in 18.0 ml of acetonitrile and 6.0 ml of water was added 1.52 g of ceric ammonium nitrate. The mixture was stirred at room temperature for 15 h, and then concentrated in vacuo. The residue was dissolved in 10 ml of dichloromethane and purified via column chromatography on a Biotage Horizon 65i column eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 100% ethyl acetate in hexanes (over 10 column volumes), and held at 100% ethyl acetate for 2 column volumes to remove all the impurities. The column was then flushed with methanol (5 column volumes) to provide the title compound (242 mg, 52%) as a white solid. Mass spectrum (ESI) 419.1 (M+1).

Provenance & Evidence