Hydrogen Peroxide → Benzoic Acid

HRID 1866163Notes

Reaction equation

HRID 1866163 reaction equation
ClC1C=C([C@@H](O)CN(CCC2C=CC([C:26]3[CH:31]=[CH:30][C:29]([CH:32]=[O:33])=[C:28](C)[C:27]=3C)=CC=2)C(=O)OC(C)(C)C)C=CC=1.OO.Cl([O-])=[O:40].[Na+]>C(#N)C.C(OCC)(=O)C>[C:32]([OH:33])(=[O:40])[C:29]1[CH:28]=[CH:27][CH:26]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11613126HCID 11613126, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl [(2R)-2-(3-chlorophenyl)-2-hydroxyethyl][2-(4′-formyl-2′,3′-dimethyl-1,1′-biphenyl-4-yl)ethyl)carbamate in acetonitrile (2.5 ml) and pH 4 buffer solution (sodium dihydrogenphosphate) (1.3 ml) was added 30% hydrogen peroxide solution (60 μl) and 80% sodium chlorite (128 mg) below 10° C. The reaction mixture was stirred at 40° C. for 1.5 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure to give a benzoic acid product. To a solution of the product in tetrahydrofuran (1.0 ml) was added 4N hydrochloride in dioxane (1.18 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-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]-2,3-dimethyl-1,1′-biphenyl-4-carboxylic acid hydrochloride (140 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-eb0c8bfc523541b29569874fe89df8aa
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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