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

Participants

Reaction Steps

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.

Provenance & Evidence