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

HRID 1460757Notes

Reaction equation

HRID 1460757 reaction equation
C[O:2][C:3](=[O:14])[C@H:4]([CH3:13])[NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O>[CH2:6]([NH:5][C@H:4]([C:3]([OH:14])=[O:2])[CH3:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=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 mmol) of N-benzylalanine methyl ester (J. Chem. Soc. 4374 (1952)) are heated under reflux overnight with 860 ml of water. Product which has deposited is filtered off with suction and the filtrate is extracted once with tert.-butyl methyl ether. The aqueous solution is concentrated and the crystals obtained are dried over phosphorus pentoxide in a desiccator with the first crystal fraction.

Workup

  1. filtrationProduct which has deposited is filtered off with suction
  2. extractionthe filtrate is extracted once with tert.-butyl methyl ether
  3. concentrationThe aqueous solution is concentrated
  4. customthe crystals obtained
  5. dry with materialare dried over phosphorus pentoxide in a desiccator with the first crystal fraction

Sources & evidence

ORD record
ord-0fba2ccba7b041e0be2028ab812d831a
Source dataset
uspto-grants-1991_12
Patent number
US05071999

Reaction notes

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