반응 #2383

반응 방정식

4-tert-butyl-N-{6-[2-(4-hydroxyphenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

sodium hydride

tert-butyl bromoacetate

ammonium chloride

→

tert-butyl 4-{2-(6-(4-tert-butybenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy)ethoxy}phenoxyacetate

수율 92.7%

용매

dimethylformamide

dimethylformamide

반응 조건

후처리

1. 1
   온도cooling
2. 2
   workup.STIRRINGthe mixture is stirred at the same temperature for one hour
3. 3
   추출extracted with ethyl acetate
4. 4
   세척The ethyl acetate layer is washed
5. 5
   기타dried
6. 6
   기타evaporated
7. 7
   기타to remove the solvent
8. 8
   기타The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=3:1)
9. 9
   기타crystallized from ethyl acetate/diisopropyl ether

실험 절차

To a solution of 4-tert-butyl-N-{6-[2-(4-hydroxyphenoxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (200 mg) in dimethylformamide (2 ml) is added sodium hydride (60% dispersion-type, 32 mg), and the mixture is stirred at room temperature for 30 minutes. To the mixture is added a solution of tert-butyl bromoacetate (77 mg) in dimethylformamide (2 ml) under ice-cooling, and the mixture is stirred at the same temperature for one hour. The reaction solution is poured into ice-water, and treated with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate=3:1), and crystallized from ethyl acetate/diisopropyl ether to give tert-butyl 4-{2-(6-(4-tert-butybenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy)ethoxy}phenoxyacetate (225 mg ).

출처