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

HRID 2222775Notes

Reaction equation

HRID 2222775 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([NH:14]C(OC(C)(C)C)=O)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 223419012-Ethanoyloxy-5-tert-butoxycarbonylaminobenzoic acid

Product 1

HCID 13140652Acetyl-5-aminosalicylic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

The mixture of 2-ethanoyloxy-5-tert-butoxycarbonylaminobenzoic acid (1.01 g, 3.42 mmole) in TFA/CH2Cl2 (20.0 ml. 1:1 v/v) was stirred for 30 min at room temperature. After the reaction mixture was concentrated, the residue was dissolved in ether. The resulting residue was recrystallized from ethyl acetate/hexane to give 0.65 g (97% yield) of 2-ethanoyloxy-5-aminobenzoic acid as a white solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ether
  3. customThe resulting residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f444f79083534edaab4af14ffeb3d34e
Source dataset
uspto-grants-2008_05
Patent number
US07371896B2

Reaction notes

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