(S)-methyl 2-(benzylamino)propanoate → N-benzyl-L-alanine

HRID 1590134Notes

Reaction equation

HRID 1590134 reaction equation
[CH2:1]([NH:8][C@H:9]([C:11]([O:13]C)=[O:12])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O>[CH2:1]([NH:8][C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 10535780(S)-methyl 2-(benzylamino)propanoate

Product 1

HCID 723764N-benzyl-L-alanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

333 g (1.72 mol) of methyl N-benzylalaninate (J. Chem. Soc. 4374 (1952)) are refluxed overnight together with 860 ml of water. Precipitated product is filtered off with suction, and the filtrate is extracted once using tert.-butyl methyl ether. The aqueous solution is concentrated, and the crystals obtained and the first crystal fraction are dried in a desiccator over phosphorus pentoxide.

Workup

  1. filtrationPrecipitated product is filtered off with suction
  2. extractionthe filtrate is extracted once using tert.-butyl methyl ether
  3. concentrationThe aqueous solution is concentrated
  4. customthe crystals obtained
  5. dry with materialthe first crystal fraction are dried in a desiccator over phosphorus pentoxide

Sources & evidence

ORD record
ord-8a46e7c3ab4b4ba4abebdb355914f65a
Source dataset
uspto-grants-1993_04
Patent number
US05202337

Reaction notes

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