L-Methionine → N-[(2-Aminophenyl)methyl]-L-methionine

HRID 1902394Notes

Reaction equation

HRID 1902394 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[NH2:10][C@H:11]([C:16]([OH:18])=[O:17])[CH2:12][CH2:13][S:14][CH3:15].C(=O)([O-])[O-].[Na+].[Na+].[BH4-].[Na+]>O>[NH2:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH2:1][NH:10][C@H:11]([C:16]([OH:18])=[O:17])[CH2:12][CH2:13][S:14][CH3:15]

Participants

6

Reactant 4

HCID 6137L-MethionineHCID 10340Sodium CarbonateHCID 682552-AminobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 13340364N-[(2-Aminophenyl)methyl]-L-methionine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.1 mol of anthranil aldehyde, 0.1 mol of methionine and a solution of 0.1 mol of sodium carbonate in 50 ml of water was stirred for a few hours. After everything had gone into solution, 0.1 mol of sodium borohydride was added, and the mixture was stirred at room temperature for 12 hours. The reaction solution was then acidified to pH3, and the precipitate was collected and dried, yielding 85% of theory of N-(2-amino-benzyl)-methionine, m.p. 198° C. The total yield, based on the anthranilic acid starting material, was 68% of theory.

Workup

  1. additionwas added
  2. customthe precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-a394203afa7c4ba28ada684d91a0a6c7
Source dataset
uspto-grants-1982_12
Patent number
US04363766

Reaction notes

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