Benzaldehyde → N-benzylidene-D-phenylalanine methyl ester

HRID 5924

Reaction equation

HRID 5924 reaction equation
Cl.[NH2:2][C@@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:14](N(CC)CC)C.N[C@@H](C(O)=O)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[O-]S([O-])(=O)=O.[Mg+2].C(=O)C1C=CC=CC=1.Cl.C(N(CC)CC)C>>[CH3:14][O:12][C:11](=[O:13])[C@@H:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[N:2]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 6

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 71567D-PhenylalanineHCID 13000988D-phenylalanine hydrochloride

Product 1

HCID 24807472N-benzylidene-D-phenylalanine methyl ester

Procedure

To a suspension of 1.0 eq D-phenylalanine HCl (1.6 g, 7.4 mmol) was added 1.0 eq triethylamine to dissolve the D-phenylalanine. To this solution was added 1 equiv. of MgSO4 followed by the addition of 1.0 eq benzaldehyde, the reaction was stirred overnight at room temperature under N2 atmosphere. The reaction mixture was sripped of solvent and pumped on the residue contained a good deal of triethylamine hydrochloride which was removed by dissolving the product in THF and filtering out the TEA.HCl. The crude benzylidene looked fine by NMR and was all taken on in the next step.

Workup

  1. customwas removed
  2. dissolutionby dissolving the product in THF
  3. filtrationfiltering out the TEA

Sources & evidence

ORD record
ord-7a7c4c7f1f2e40e19f403a27972819ca
Source dataset
uspto-grants-1993_09
Patent number
US05246944

Linked notes

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