تفاعل #70073
ord-701a9bd0582d4b59bcee3196b82aab71
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
ظروف التفاعل
المعالجة
- 1درجة الحرارةwas heated
- 2درجة الحرارةunder reflux for 6 hr under a nitrogen atmosphere
- 3درجة الحرارةThe reaction mixture was cooled
- 4ترشيحfiltered
- 5غسيلthe cake was washed with acetonitrile (35 mL)
- 6تركيزThe filtrate was concentrated under reduced pressure at 35° C.
- 7أخرىlower to give a crude product
- 8أخرىThe crude product was purified by silica gel column chromatography (eluent: toluene/ethyl acetate (100:0-4:1))
- 9تركيزthe fraction was concentrated
- 10workup.ADDITIONTo the residue was added chloroform (about 30 ml)
- 11تركيزthe mixture was concentrated
- 12أخرىThe residue was dried under reduced pressure in a bath at 40° C.
الإجراء التجريبي
A mixture of 5-[4′-(bromomethyl)biphenyl-2-yl]-1-(p-methoxybenzyl)-1H-tetrazole (compound 5a, 9.25 g, 21.2 mmol), acetonitrile (107 ml), methyl 2-(tert-butoxycarbonylamino)-3-nitrobenzoate (compound 19a, 6.43 g, 21.7 mmol) and potassium carbonate (3.00 g, 21.7 mmol) was heated under reflux for 6 hr under a nitrogen atmosphere. The reaction was monitored by TLC (eluent: toluene/ethyl acetate (4:1)). The reaction mixture was cooled, and filtered, and the cake was washed with acetonitrile (35 mL). The filtrate was concentrated under reduced pressure at 35° C. or lower to give a crude product. The crude product was purified by silica gel column chromatography (eluent: toluene/ethyl acetate (100:0-4:1)), and the fraction was concentrated. To the residue was added chloroform (about 30 ml), and the mixture was concentrated. The operations were repeated four times. The residue was dried under reduced pressure in a bath at 40° C. to give methyl 2-(N-tert-butoxycarbonyl-N-{(2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate (compound 20a) as a yellowish brown amorphous solid (9.83 g (71.1%)).