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

Participants

Reaction Steps

To a solution of methyl 2-(N-tert-butoxycarbonyl-N-{(2′-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate (compound 20b, 11.93 g, 19.2 mmol) in methanol (15 mL) was added 2NHCl-MeOH (30 mL) under ice-cooling, and the mixture was stirred at the same temperature for 2 hr, and then overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and to the residue were added methanol and diisopropyl ether. The resulting crystals were collected by filtration, washed with diisopropyl ether and hexane, and dried under reduced pressure to give methyl 2-[({2′-[1-benzyl-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate (compound 21b) (8.64 g, 86%) as yellow crystals.

Provenance & Evidence