Benzaldehyde → N-benzylidene-D-phenylalanine methyl ester

HRID 5924

반응식

HRID 5924 반응식
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

참가 물질

7

반응물 6

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

생성물 1

HCID 24807472N-benzylidene-D-phenylalanine methyl ester

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-7a7c4c7f1f2e40e19f403a27972819ca
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246944

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