N-Benzylglycine ethyl ester → 2-(Benzylamino)acetic acid

HRID 1645975Notes

Reaction equation

HRID 1645975 reaction equation
C([O:3][C:4](=[O:14])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C>O>[CH2:7]([NH:6][CH2:5][C:4]([OH:14])=[O:3])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 80908N-Benzylglycine ethyl ester

Product 1

HCID 869652-(Benzylamino)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

225.8 g (1.17 mol) of N-benzylglycine ethyl ester (J. Am. Chem. Soc. 72, 1238 (1950)) are heated under reflux overnight in 600 ml of water. Product which has crystallized out is filtered off with suction and the filtrate is extracted once with tert.-butyl methyl ether. The aqueous phase is concentrated and the crystals obtained are dried over phosphorus pentoxide in a desiccator together with the product filtered off.

Workup

  1. customProduct which has crystallized out
  2. filtrationis filtered off with suction
  3. extractionthe filtrate is extracted once with tert.-butyl methyl ether
  4. concentrationThe aqueous phase is concentrated
  5. customthe crystals obtained
  6. dry with materialare dried over phosphorus pentoxide in a desiccator together with the product
  7. filtrationfiltered off

Sources & evidence

ORD record
ord-641f836f4b394ef1966549dbc5638b23
Source dataset
uspto-grants-1993_01
Patent number
US05177210

Reaction notes

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