Hydrogen Peroxide → Benzoic Acid

HRID 1823103Notes

Reaction equation

HRID 1823103 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-e004054d7c8c43d3be5b3e302844d181
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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