Benzaldehyde → HCID 11437078, compound

HRID 1841652Notes

Reaction equation

HRID 1841652 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S([O-])([O-])(=O)=O.[Mg+2].C(N(CC)CC)C>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[N:6]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 11437078HCID 11437078, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-phenylalanine methyl ester hydrochloride (4.31 g), benzaldehyde (2.05 ml), anhydrous magnesium sulfate (5.19 g) and triethylamine (2.90 ml) were added to methylene chloride (200 ml), and the mixture was stirred overnight at room temperature. The solid was filtered off from the reaction solution, and the solvent was distilled off under reduced pressure. Then, ethyl acetate (150 ml) was added to the residue. The solid was separated again by filtration, and the solvent was distilled off under reduced pressure to obtain desired N-(phenylmethylene)-L-phenylalanine methyl ester (5.18 g) in a yield of 97.0%.

Workup

  1. filtrationThe solid was filtered off from the reaction solution
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThen, ethyl acetate (150 ml) was added to the residue
  4. customThe solid was separated again by filtration
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a09a88aedb594b9fb22880f2f73eccc3
Source dataset
uspto-grants-2004_01
Patent number
US06683214B2

Reaction notes

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