Trifluoroacetic acid → N-[3-(hydroxyiminomethyl)benzyl]succinamic acid

HRID 2112435Notes

Reaction equation

HRID 2112435 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:29])[CH2:14][CH2:15][C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]=[N:27][OH:28])[CH:21]=1)=[O:17])(C)(C)C>ClCCl>[OH:28][N:27]=[CH:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][NH:18][C:16](=[O:17])[CH2:15][CH2:14][C:13]([OH:29])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 76573399N-[3-((hydroxyimino)methyl)benzyl]succinamic acid tert-butyl ester

Product 1

HCID 76573391N-[3-(hydroxyiminomethyl)benzyl]succinamic acidYield 145%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (7 ml) was added to a solution of crude N-[3-((hydroxyimino)methyl)benzyl]succinamic acid tert-butyl ester (249 mg, 0.81 mmol) in dichloromethane (7 ml). The reaction mixture was stirred for 55 min at room temperature. The solvent was removed in vacuo. The residue was redissolved in dichloromethane (50 ml). The solvent was removed in vacuo. The latter procedure was repeated twice to give 294 mg of crude N-[3-(hydroxyiminomethyl)benzyl]succinamic acid, which was used in the next step without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was redissolved in dichloromethane (50 ml)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-eaba9fadf71b420e93f45f8f4a76b0d3
Source dataset
uspto-grants-2009_04
Patent number
US07524813B2

Reaction notes

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