反应 #6020

ord-7a7c4c7f1f2e40e19f403a27972819ca

反应方程式

O=S(=O)([O-])[O-].[Mg+2]
MgSO4
CCN(CC)CC.Cl
triethylamine hydrochloride
Cl.N[C@H](Cc1ccccc1)C(=O)O
D-phenylalanine HCl
CCN(CC)CC
triethylamine
O=Cc1ccccc1
benzaldehyde
N[C@H](Cc1ccccc1)C(=O)O
D-phenylalanine
COC(=O)[C@@H](Cc1ccccc1)N=Cc1ccccc1
N-benzylidene-D-phenylalanine methyl ester

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他was removed
  2. 2
    workup.DISSOLUTIONby dissolving the product in THF
  3. 3
    过滤filtering out the TEA

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US05246944uspto-grants-1993_09