反应详情

0.31 ml (3.57 mmol) of oxalyl chloride and a catalyic amount of dimethyl-formamide were added, with ice-cooling, to a solution of 350 mg (1.19 mmol) of 3-(2,4-dimethoxyphenyl)nonanoic acid (prepared as described in Preparation 42B), in 7 ml of methylene chloride and the reaction temperature was raised to room temperature at once. The resulting mixture was then stirred for 50 minutes. The solvent and an excess of the reagent were removed by distillation under reduced pressure, and the resulting residue was dissolved in 7 ml of methylene chloride. 0.48 ml (5.95 mmol) of pyridine were added to the solution, followed by 206 mg (1.07 mmol) of 2-t-butyl-5-carbamoylaniline (prepared as described in Preparation 38), all with ice-cooling, and the resulting mixture was stirred at the same temperature for 30 minutes. At the end of this time, the reaction mixture was diluted with diethyl ether, and the diluted solution was washed with 1N aqueous hydrochloric acid, with a 0.5N aqueous solution of sodium hydroxide, with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 25 g of silica gel using a gradient elution method, with mixtures of methylene chloride and methanol ranging from 100:2 to 100:4 by volume as the eluent, to give 433 mg (yield 86%) of the title compound as crystals, melting at 152°-153° C. (from methylene chloride-diethyl ether).

1. customThe solvent and an excess of the reagent were removed by distillation under reduced pressure
2. dissolutionthe resulting residue was dissolved in 7 ml of methylene chloride
3. temperatureall with ice-cooling
4. stirringthe resulting mixture was stirred at the same temperature for 30 minutes
5. washthe diluted solution was washed with 1N aqueous hydrochloric acid, with a 0.5N aqueous solution of sodium hydroxide, with water and with a saturated aqueous solution of sodium chloride, in that order
6. dry with materialafter which it was dried over anhydrous magnesium sulfate
7. customThe solvent was removed by distillation under reduced pressure
8. customthe resulting residue was purified by column chromatography through 25 g of silica gel using
9. washa gradient elution method