N-[4-(benzyloxy)benzoyl]glycine methyl ester → {[4-(Benzyloxy)phenyl]formamido}acetic acid

HRID 53082Notes

Reaction equation

HRID 53082 reaction equation
FC1C([O:8][C:9](=[O:28])[CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)=C(F)C(F)=C(F)C=1F.COC(=O)CNC(=O)C1C=CC(OCC2C=CC=CC=2)=CC=1>[OH-].[Na+]>[C:21]1([CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([NH:11][CH2:10][C:9]([OH:28])=[O:8])=[O:27])=[CH:14][CH:15]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 27681983N-[4-(benzyloxy)benzoyl]glycine methyl esterHCID 53980088N-(4-(Phenylmethoxy)benzoyl)glycine pentafluorophenyl ester

Product 1

HCID 23931762{[4-(Benzyloxy)phenyl]formamido}acetic acidYield 47%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N-(4-(Phenylmethoxy)benzoyl)glycine pentafluorophenyl ester. N-(4-(Phenyl-methoxy)benzoyl)glycine methyl ester (14.75 g, 49.2 mmol) was boiled under reflux with methanolic sodium hydroxide (1M) (80 mL) for 2 h. The solvent was evaporated under reduced pressure. The residue was dissolved in water and was acidified by addition of aqueous hydrochloric acid. The suspension was extracted with ethyl acetate. The extract was washed with saturated brine and was dried with anhydrous magnesium sulphate. The solvent was evaporated under reduced pressure to give N-(4-(phenylmethoxy)benzoyl)glycine (6.59 g, 47%). Dicyclohexylcarbodiimide (720 mg, 3.5 mmol) was added to N-(4-(phenylmethoxy)benzoyl)glycine (100 g, 3.5 mmol) in dry tetrahydrofuran (100 mL) and the mixture was taken to 0° C. Pentafluorophenol (640 g, 3.5 mmol) was added dropwise and the mixture was stirred for 17 h at 0° C. The suspension was filtered and the solvent was evaporated from the filtrate under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and was washed with saturated aqueous sodium hydrogen carbonate (2×75 mL), with aqueous sulphuric acid (10%) and with water. The solution was dried with anhydrous magnesium sulphate and the solvent was evaporated under reduced pressure to give N-(4-(phenylmethoxy)benzoyl)glycine pentafluorophenyl ester (Intermediate B) (1.5 g, 95%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. additionwas acidified by addition of aqueous hydrochloric acid
  4. extractionThe suspension was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialwas dried with anhydrous magnesium sulphate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cf6c3e93989743d7af687c04dbcdb52d
Source dataset
uspto-grants-1997_04
Patent number
US05618528

Reaction notes

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