Pyridine → HCID 57005544, compound

Participants

Reaction Steps

To a solution of (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(4-phenylcyclohexylmethyl)butanoic acid (3.65 g, 0.009 mol) in dichloromethane (20 mL) at 25° C. is added via syringe pyridine (0.87 g, 0.011 mol) followed by pentafluorophenyl trifluoroacetate (3.1 g, 0.011 mol). The mixture is stirred for 6 h, diluted with dichloromethane and washed with 0.1 M aqueous HCl, 1 M aqueous sodium carbonate, saturated aqueous sodium chloride and dried over sodium sulfate. Concentration in vacuo followed by chromatography on silica gel with hexanes-EtOAc (2:1) as eluent gives 3.05 g (60%) of pentafluorophenyl (2R,3S)-3-(formyl-2-tetrahydropyranyloxyamino)-2-(4-phenylcyclohexylmethyl)butanoate as an oil.

Provenance & Evidence