Hydrogen Peroxide → Benzoic Acid

Temperature

20 °C

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).

1. washwashed with water and brine
2. dry with materialdried over magnesium sulfate
3. customevaporated under reduced pressure
4. customThe residue was purified by column chromatography on silica gel (chloroform/methanol=15/1)

ORD record

ord-137deca7d1cb4e58b011530cc20abff9

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417060B2