Reaktion #70076

Reaktionsgleichung

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

Ausbeute 81.7%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 6 hr under argon stream
3. 3
   Temperaturthe mixture was heated
4. 4
   Temperaturunder reflux for 3 hr
5. 5
   TemperaturThe reaction mixture was cooled
6. 6
   Filtrationfiltered
7. 7
   WaschenThe insoluble material was washed with chloroform
8. 8
   WaschenThe filtrate and washing
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    SonstigeThe concentrated residue was purified by silica gel column (hexane→hexane:AcOEt=5:1→4:1→3:1→2:1→3:2)

Vorschrift

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.

Quelle