Sodium Hydroxide → Benzoic Acid

HRID 2220376Notes

Reaction equation

HRID 2220376 reaction equation
C(OC(N(C[C@H](O)C1C=CC=CC=1)CCC1C=CC([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]C)=[O:24])=[C:19](C3SC=CC=3)[CH:18]=2)=CC=1)=O)(C)(C)C.[OH-].[Na+]>CO>[C:23]([OH:25])(=[O:24])[C:20]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69103883HCID 69103883, compound

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 4′-[2-[(tert-butoxycarbonyl)-[(2R)-2-hydroxy-2-phenylethyl]amino]ethyl]-3-(2-thienyl)-4-bipheylcarboxylate (188 mg) in methanol (3.3 ml) was added 1N aqueous sodium hydroxide solution (1.0 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 ethyl acetate (1.0 ml) was added 4N hydrogen chloride in ethyl acetate (1.0 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-(2-thienyl)-4-biphenylcarboxylic acid hydrochloride (139 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-e7800ecd06ee4df1be433138b8291580
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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