반응 #70076

반응 방정식

potassium carbonate

1-benzyl-5-[4′-(bromomethyl)biphenyl-2-yl]-1H-tetrazole

compound 5b

1-benzyl-5-[4′-(bromomethyl)biphenyl-2-yl]-1H-tetrazole

methyl 2-(tert-butoxycarbonylamino)-3-nitrobenzoate

compound 19a

methyl 2-(tert-butoxycarbonylamino)-3-nitrobenzoate

potassium carbonate

→

methyl 2-(N-tert-butoxycarbonyl-N-{(2′-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate

수율 81.7%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux for 6 hr under argon stream
3. 3
   온도the mixture was heated
4. 4
   온도under reflux for 3 hr
5. 5
   온도The reaction mixture was cooled
6. 6
   여과filtered
7. 7
   세척The insoluble material was washed with chloroform
8. 8
   세척The filtrate and washing
9. 9
   농축concentrated under reduced pressure
10. 10
    기타The concentrated residue was purified by silica gel column (hexane→hexane:AcOEt=5:1→4:1→3:1→2:1→3:2)

실험 절차

A mixture of 1-benzyl-5-[4′-(bromomethyl)biphenyl-2-yl]-1H-tetrazole (compound 5b, 9.82 g, 24 mmol), methyl 2-(tert-butoxycarbonylamino)-3-nitrobenzoate (compound 19a, 7.32 g, 24.7 mmol) and potassium carbonate (3.68 g, 26.7 mmol) in acetonitrile (100 mL) was heated under reflux for 6 hr under argon stream. To the reaction mixture was added potassium carbonate (1.34 g), and the mixture was heated under reflux for 3 hr. The reaction mixture was cooled and filtered. The insoluble material was washed with chloroform. The filtrate and washing were combined, and concentrated under reduced pressure. The concentrated residue was purified by silica gel column (hexane→hexane:AcOEt=5:1→4:1→3:1→2:1→3:2) to give methyl 2-(N-tert-butoxycarbonyl-N-{(2′-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate (compound 20b) (12.17 g, 81%) as a yellow amorphous solid.

출처