Lithium Hydroxide → N-[(4-Hydroxybenzoyl)acetyl]glycine

HRID 1178070

Reaction equation

HRID 1178070 reaction equation
[Li+].[OH-].C([O:5][C:6](=[O:20])[CH2:7][NH:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)C>C1COCC1.CO.O>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][C:9]([NH:8][CH2:7][C:6]([OH:20])=[O:5])=[O:19])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 102641582-[3-(4-Hydroxyphenyl)propionylamino]acetic acid ethyl ester

Product 1

HCID 577651N-[(4-Hydroxybenzoyl)acetyl]glycineYield 89.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (56 mg, 2.33 mmol) was added at room temperature to a stirred solution of [3-(4-hydroxy-phenyl) propionylamino]-acetic acid ethyl ester (151 mg, 0.6 mmol) in THF:MeOH:H2O (3:1:1, 5 mL). The resulting mixture was stirred at room temperature for five hours. The MeOH and THF were then evaporated and the residue was diluted with water (2 mL), acidified with 20% aqueous HCl and extracted with EtOAc. The organic layer was washed with saturated brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford 120 mg (89.55% yield) of [3-(4-hydroxy-phenyl) propionylamino]-acetic acid as a pale white solid (120 mg). LCMS purity: 90.42%.

Workup

  1. customThe MeOH and THF were then evaporated
  2. additionthe residue was diluted with water (2 mL)
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e8847b5f5e734ea3abe487cf08b655d2
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Linked notes

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