Citric Acid → HCID 22914691, compound

HRID 1377669Notes

Reaction equation

HRID 1377669 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:6][C:5]=1[O:22][CH3:23].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:18]([O:17][C:15]([NH:14][CH2:13][CH2:12][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:24])=[O:2])=[C:5]([O:22][CH3:23])[CH:6]=1)=[O:16])([CH3:20])([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 54473187HCID 54473187, compound

Product 1

HCID 22914691HCID 22914691, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3-(t-Butyloxycarbonylamino)-propyloxy)-2-methoxybenzoic acid methyl ester (2.63 g, 7.76 mmol) from Step 2 was dissolved in MeOH (25 mL) and heated with 1N NaOH (15 mL, 15 mmol)) at 50° C. for 18 h. The reaction was cooled to ambient temperature and 5% aqueous citric acid (10 mL) was added. The mixture was extracted with EtOAc (3×75 mL). The combined EtOAc phases were washed with water (2×50 mL) and brine (50 mL), dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-(3-(t-butyloxycarbonylamino)propyloxy)-2-methoxybenzoic acid as a white foam (95% yield).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×75 mL)
  2. washThe combined EtOAc phases were washed with water (2×50 mL) and brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ab95dd1aa4134c61919b355fbd4ba1c5
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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