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

HRID 1975001Notes

Reaction equation

HRID 1975001 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]([O:12]CC)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O>[CH2:1]([NH:8][CH2:9][C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 ethyl N-benzylglycinate (J. Am. Chem. Soc. 72, 1238 (1950)) are refluxed overnight in 600 ml of water. The product which has crystallised out is filtered off with suction and the filtrate is extracted once using tert.-butyl methyl ether. The aqueous phase is concentrated and the crystals obtained together with the product which has been faltered of fare dried in a desiccator over phosphorus pentoxide.

Workup

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

Sources & evidence

ORD record
ord-5f99d106f7fe4fc69386256948d22c0d
Source dataset
uspto-grants-1994_02
Patent number
US05284855

Reaction notes

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