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

HRID 1590130Notes

Reaction equation

HRID 1590130 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 filtered off are 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. filtrationhas been filtered off
  7. dry with materialare dried in a desiccator over phosphorus pentoxide

Sources & evidence

ORD record
ord-5d7786d2a327470dbfa464f80287a3e7
Source dataset
uspto-grants-1993_04
Patent number
US05202337

Reaction notes

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