Citric Acid → HCID 22914662, compound

HRID 1377714Notes

Reaction equation

HRID 1377714 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[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[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[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 22914707HCID 22914707, compound

Product 1

HCID 22914662HCID 22914662, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-methoxy-4-(1-tert-butyloxycarbonyl-3-piperidinyloxy)benzoate from Step 3 above (1.35 g, 3.69 mmol) in methanol (25 mL) was added 2N NaOH (9.2 mL, 18.5 mmol). The reaction mixture was heated to reflux for 30 minutes and then cooled in an ice water bath. The solution was acidified with 5% citric acid and 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, and the solvent was evaporated to give 2-methoxy-4-(1-tert-butyloxycarbonyl-3-piperidinyloxy)benzoic acid as a white solid which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-8305b06942d543a08b74837751340dfc
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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