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

HRID 2415649Notes

Reaction equation

HRID 2415649 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

N-benzylglycine ethyl ester (97.0 g, 503 mmol) was refluxed in 260 mL of water (with 480 mg of KOH, 0.5 wt %) overnight. The reaction mixture was filtered. The filtercake was washed with chloroform and dried under vacuum. The filtrate was extracted with tert-butyl methyl ether. The aqueous phase from this extraction was separated, adjusted to pH 2 with 6M HCl, and then concentrated in vacuo. The residue was filtered and this filtercake was washed with chloroform and dried under vacuum. The two filtercakes were combined.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washThe filtercake was washed with chloroform
  3. customdried under vacuum
  4. extractionThe filtrate was extracted with tert-butyl methyl ether
  5. extractionThe aqueous phase from this extraction
  6. customwas separated
  7. concentrationconcentrated in vacuo
  8. filtrationThe residue was filtered
  9. washthis filtercake was washed with chloroform
  10. customdried under vacuum

Sources & evidence

ORD record
ord-65b14e303a614de08b6b561c28984ace
Source dataset
uspto-grants-2004_11
Patent number
US06821964B2

Reaction notes

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