Acetic Acid → HCID 54473187, compound

HRID 1377668Notes

Reaction equation

HRID 1377668 reaction equation
[CH3:1][O:2][C:3](=[O:23])[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[OH:22].[H-].[Na+].IC.[C:28](O)(=O)C>CN(C=O)C>[CH3:1][O:2][C:3](=[O:23])[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]([CH3:19])([CH3:20])[CH3:21])=[O:16])=[CH:6][C:5]=1[O:22][CH3:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3316729HCID 3316729, compound

Product 1

HCID 54473187HCID 54473187, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 4-(3-(t-butyloxycarbonylamino)propyloxy)-2-hydroxybenzoic acid methyl ester (3.0 g, 9.2 mmol) from Step 1 in dry DMF (25 mL) was added sodium hydride (0.39 g of a 60% suspension in mineral oil, 9.7 mmol). The reaction was stirred at 0° C. for 1 h, when iodomethane (1.0 mL, 16 mmol) was added. The reaction was then warmed to ambient temperature. After 24 h, acetic acid (1 mL) was added and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (150 mL) and washed with saturated aqueous NaHCO3 (3×100 mL). The EtOAc layer was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 3:7 EtOAc:hexanes as eluant. 4-(3-(t-Butyloxycarbonylamino)propyloxy)-2-methoxybenzoic acid methyl ester was obtained as an oil (85% yield).

Workup

  1. temperatureThe reaction was then warmed to ambient temperature
  2. waitAfter 24 h
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc (150 mL)
  5. washwashed with saturated aqueous NaHCO3 (3×100 mL)
  6. dry with materialThe EtOAc layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-54d6ce268f99421f8dde438d3c369f0b
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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