반응 #70075

반응 방정식

methyl 2-[({2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate

compound 21a

methyl 2-[({2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate

tin(II) chloride dihydrate

→

methyl 2-[({2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-aminobenzoate

수율 75.9%

용매

methanol

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux for 2 hr
3. 3
   농축The reaction mixture was concentrated under reduced pressure
4. 4
   workup.ADDITIONto the concentrated residue were added saturated aqueous sodium hydrogen carbonate and ethyl acetate
5. 5
   여과filtered
6. 6
   세척the insoluble material was washed with ethyl acetate
7. 7
   세척The filtrate and washing
8. 8
   농축concentrated under reduced pressure
9. 9
   추출The concentrated solution was extracted with ethyl acetate
10. 10
    여과filtered
11. 11
    농축The filtrate was concentrated under reduced pressure
12. 12
    기타the concentrated residue was purified by silica gel column (hexane→hexane:AcOEt=4:1→2:1→3:2)

실험 절차

A mixture of methyl 2-[({2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate (compound 21a, 2.73 g, 4.96 mmol) and tin(II) chloride dihydrate (4.48 g, 19.9 mmol) in methanol (60 mL) was heated under reflux for 2 hr. The reaction mixture was concentrated under reduced pressure, and to the concentrated residue were added saturated aqueous sodium hydrogen carbonate and ethyl acetate. The mixture was stirred for 1 hr, and filtered, and the insoluble material was washed with ethyl acetate. The filtrate and washing were combined, and concentrated under reduced pressure. The concentrated solution was extracted with ethyl acetate. The ethyl acetate solution of the resultant product was dried magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the concentrated residue was purified by silica gel column (hexane→hexane:AcOEt=4:1→2:1→3:2) to give methyl 2-[({2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-aminobenzoate (compound 22a) (1.96 g, 70%) as a brown amorphous solid.

출처