Lithium Hydroxide → m-Hydroxyhippuric acid

HRID 1178046Notes

Reaction equation

HRID 1178046 reaction equation
[Li+].[OH-].C([O:5][C:6](=[O:18])[CH2:7][NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)C>C1COCC1.CO>[OH:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[C:9]([NH:8][CH2:7][C:6]([OH:18])=[O:5])=[O:17]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 13022859HCID 13022859, compound

Product 1

HCID 450268m-Hydroxyhippuric acidYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (75 mg in 2 mL water) was added to (3-hydroxy-benzoyl amino)-acetic acid ethyl ester (100 mg, 0.45 mmol) in a mixture of THF and MeOH mixture. This was followed by the addition of to the reaction mixture. The resulting mixture was stirred at room temperature overnight. The THF and MeOH were then evaporated under reduced pressure and the resulting residue was acidified to pH 2 using 10% citric acid solution. The product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford (3-hydroxy-benzoyl amino)-acetic acid in 89% yield. 1H NMR (DMSO-D6): δ 12.4 (s, 1H), 9.6 (s, 1H), 8.7 (t, 1H), 7.2 (d, 3H), 6.9 (m, 1H), 4.0 (d, 2H).

Workup

  1. additionThis was followed by the addition of to the reaction mixture
  2. customThe THF and MeOH were then evaporated under reduced pressure
  3. extractionThe product was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1ac14ddb439426f8ce7dd9cb070cd17
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

Loading…