Methyl alpha-amino-p-methoxycarbonylmethylphenylacetate → (RS)-alpha-amino-p-carboxymethylphenylacetic acid

HRID 1289240Notes

Reaction equation

HRID 1289240 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16]C)=[O:15])=[CH:9][CH:8]=1)[C:3]([O:5]C)=[O:4]>Cl>[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4]

Participants

3

Reactant 1

HCID 54294376Methyl alpha-amino-p-methoxycarbonylmethylphenylacetate

Product 1

HCID 18925125(RS)-alpha-amino-p-carboxymethylphenylacetic acidYield 99%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of methyl α-amino-p-methoxycarbonylmethylphenylacetate (2.3 g, 7 mmol) in 60 ml of 6N HCl was refluxed for 12 hours. After cooling white needles were collected. The aqueous layers were extracted with ethyl acetate. The organic layers were evaporated and the solids combined to give (RS)-α-amino-p-carboxymethylphenylacetic acid (1.45 g, 83%);

Workup

  1. temperaturewas refluxed for 12 hours
  2. temperatureAfter cooling white needles
  3. customwere collected
  4. extractionThe aqueous layers were extracted with ethyl acetate
  5. customThe organic layers were evaporated

Sources & evidence

ORD record
ord-381463ce4d2a42529a84fb8a8dcb4c07
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

Loading…