Citric Acid → HCID 22914647, compound

HRID 1377709Notes

Reaction equation

HRID 1377709 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]2)[CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]2)[CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 22914645HCID 22914645, compound

Product 1

HCID 22914647HCID 22914647, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-methoxy-4-(1-tert-butyloxycarbonyl-3-pyrrolidinyloxy)benzoate from Step 2 above (2.26 g, 6.43 mmol) in methanol (25 mL) was added 2N NaOH (16 mL, 32.2 mmol). The reaction mixture was refluxed for 30 minutes and cooled in a ice water bath. The solution was acidified with 5% citric acid, then the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water (2×75 mL). The organic layer was dried (MgSO4), filtered, then the solvent was evaporated to give 2-methoxy-4-(1-tert-butyloxycarbonyl-3-pyrrolidinyloxy)benzoic acid as a white solid which was used without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. temperaturecooled in a ice water bath
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water (2×75 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9b461233842d4f7f9c4cb655a74ef179
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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