Benzaldehyde → N-benzylidene histidine methyl ester

HRID 1906871Notes

Reaction equation

HRID 1906871 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH2:6][C:7]1[N:11]=[CH:10][NH:9][CH:8]=1)[NH2:5].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH2:6][C:7]1[N:11]=[CH:10][NH:9][CH:8]=1)[N:5]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 178501495HCID 178501495, compound

Product 1

HCID 178501395N-benzylidene histidine methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Histidine methyl ester, 185 mg (1 mmole), is treated with 1.06 g (1 mmole) of benzaldehyde in 25 ml of CHCl3 for 3 hours. MgSO4, 0.2 g, is added for the last hour. The mixture is filtered and the solvent is evaporated, to leaving compound 2.I as a residue.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-84cc1e002fb8449588e025237d26e5b6
Source dataset
uspto-grants-1987_03
Patent number
US04654359

Reaction notes

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