Hydrogen Peroxide → Benzoic Acid

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl [2-[4′-formyl-3′-[isopropyl(methyl)amino]-4-biphenylyl]ethyl][(2R)-2-hydroxy-2-phenylethyl]carbamate (310 mg) in acetonitrile (3.5 ml) and pH 4 buffer solution (sodium dihydrogenphosphate) (1.6 ml) were added 30% hydrogen peroxide solution (60 μl) and 80% sodium chlorite (110 mg) below 10° C. The reaction mixture was stirred at 20° C. for 10 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform/methanol=15/1) to give a benzoic acid product (35 mg). To a solution of the product in ethyl acetate (0.5 ml) was added 4N hydrogen chloride in ethyl acetate (0.5 ml), and the mixture was stirred at room temperature for 12 hours. The resultant solid was collected by filtration and dried to give 4′-[2-[[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-[isopropyl(methyl)amino]-4-biphenylcarboxylic acid dihydrochloride (23 mg).

Provenance & Evidence