Citric Acid → HCID 22914678, compound

HRID 1377710Notes

Reaction equation

HRID 1377710 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]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][CH2:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)[CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 54140496HCID 54140496, compound

Product 1

HCID 22914678HCID 22914678, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-methoxy-4-(1-tert-butyloxycarbonyl-4-piperidinylmethoxy)benzoate from Step 2 above (750 mg, 1.98 mmol) in methanol (10 mL) was added 2N NaOH (4.95 mL, 9.90 mmol). The reaction mixture was refluxed for 30 minutes then cooled in a ice water bath. The solution was acidified with 5% citric acid and the solvent evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water (2×25 mL). The organic layer was dried (MgSO4), filtered, then the solvent was evaporated to give 2-methoxy-4-(1 -tert-butyloxycarbonyl-4-piperidinylmethoxy)benzoic acid as a white solid which was used without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. temperaturethen cooled in a ice water bath
  3. customthe solvent evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water (2×25 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dc7cc44214384e2a836d41fac2d4b5fe
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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