Benzaldehyde → N-benzylidene-D-phenylalanine methyl ester

HRID 2081187

Reaktionsgleichung

Reaktionsgleichung von HRID 2081187
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

Komponenten

7

Edukt 6

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

Produkt 1

HCID 24807472N-benzylidene-D-phenylalanine methyl ester

Versuchsvorschrift

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 stripped 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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-cd29c541c53347718afc357569e07a57
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05183810

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