Sodium Hydroxide → Benzoic Acid

HRID 1866144Notes

Reaction equation

HRID 1866144 reaction equation
C(OC(N(C[C@@H](C1C=CC=C(Cl)C=1)O)CCC1C=CC(O[C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=2)=CC=1)=O)(C)(C)C.[OH-].[Na+]>C(O)C>[C:20]([OH:22])(=[O:21])[C:19]1[CH:24]=[CH:25][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24823622HCID 24823622, compound

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 4-[4-[2-[(tert-butoxycarbonyl)[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenoxy]benzoate (183 mg) in ethanol (1.2 ml) was added 1N aqueous sodium hydroxide solution (0.6 ml), and the mixture was stirred at 40° C. for 3 hours. The solvent was removed by evaporation, and the aqueous solution was acidified with 1N aqueous hydrochloride solution and extracted with ethyl acetate (30 ml×2). The combined organic layers were 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 (2.0 ml) was added 4N hydrochloride in 1,4-dioxane (1.0 ml), and the mixture was stirred at room temperature for 12 hours. The resulting solid was collected by filtration and dried to give 4-[4-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]-phenoxy]benzoic acid hydrochloride (127 mg).

Workup

  1. customThe solvent was removed by evaporation
  2. extractionextracted with ethyl acetate (30 ml×2)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8b57512e16634ac990b4f48cf21ee7cd
Source dataset
uspto-grants-2009_12
Patent number
US07629366B2

Reaction notes

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