Acetyl chloride → 2-Ethanoyloxy-5-tert-butoxycarbonylaminobenzoic acid

HRID 584869Notes

Reaction equation

HRID 584869 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([OH:18])=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](Cl)(=[O:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:19]([O:18][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 103775625-(N-tert-Butoxycarbonylamino)salicylic Acid

Product 1

HCID 223419012-Ethanoyloxy-5-tert-butoxycarbonylaminobenzoic acidYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-tert-butoxycarbonylamino-2-hydroxybenzoic acid (1.02 g, 4.02 mmole) in DMF (20.0 ml) was added with acetyl chloride (39 mg, 4.83 mmole) and potassium carbonate (555 mg, 4.02 mmole). The reaction mixture was stirred for 4 hr at room temperature. After the reaction mixture was concentrated, the residue was dissolved in ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was recrystallized from ethyl acetate/hexane to give 0.62 g (52% yield) of 2-ethanoyloxy-5-tert-butoxycarbonylaminobenzoic acid as a white solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customAfter evaporation of the solvent
  6. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ae905d21ae4948efa3b1e5e5206e6565
Source dataset
uspto-grants-2005_08
Patent number
US06927303B2

Reaction notes

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