Isotretinoin amido derivative, preparation method thereof and applications thereof
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Embodiment 1
[0053] Embodiment 1: the synthesis of p-(isotretinoin amido) methyl benzoate
[0054] In a 250ml three-necked flask, add 4-dimethylaminopyridine (DMAP) (0.1g, 0.8mmol), p-toluenesulfonic acid (0.14g, 0.8mmol), add CH 2 Cl 2 110ml, then added isotretinoin (2.4g, 8mmol), methyl p-aminobenzoate (1.21g, 8.0mmol), stirred at room temperature for 10min, then added DCC (1.82g, 8.8mmol), stirred at 10°C for about 4 hours, stop the reaction. The above reactions were carried out under the protection of nitrogen and away from light. The above reaction mixture was placed at 0-5°C for about 12 hours, taken out and filtered, and the filtrate was rotary evaporated to obtain a crude product, which was separated by column chromatography (200-300 mesh silica gel, eluent: ethyl acetate:petroleum ether 1:15 ( V / V) ~ 1:10 (V / V)), gradient elution, and the resulting product was recrystallized from ethanol to obtain the reaction product (3.02g). The molecular mass of the reaction product is 433....
Embodiment 2
[0055] Embodiment 2: the synthesis of p-(isotretinoin amido) ethyl benzoate
[0056] In a 250ml three-necked flask, add 4-dimethylaminopyridine (DMAP) (0.1g, 0.8mmol), p-toluenesulfonic acid (0.14g, 0.8mmol), add CH 2 Cl 2 110ml, then added isotretinoin (2.4g, 8mmol), ethyl p-aminobenzoate (1.4g, 8.4mmol), stirred at room temperature for about 15min, then added DCC (1.87g, 9.1mmol), 40°C Stir and reflux for about 3 hours to stop the reaction. The above reactions were carried out under the protection of nitrogen and away from light. The above reaction mixture was placed at 0-5°C for about 12 hours, taken out and filtered, and the filtrate was rotary evaporated to obtain a crude product, which was separated by column chromatography (200-300 mesh silica gel, eluent: ethyl acetate:petroleum ether 1:20 ( V / V)), and the resulting product was recrystallized from ethanol to obtain a reaction product (3.58 g). The molecular mass of reaction product is 447.62, proton nuclear magneti...
Embodiment 3
[0057] Embodiment 3: the synthesis of p-(isotretinoin amido) propyl benzoate
[0058] In a 250ml three-necked flask, add 4-dimethylaminopyridine (DMAP) (0.12g, 0.96mmol), p-toluenesulfonic acid (0.17g, 0.96mmol), add CH 2 Cl 2 110ml, then added isotretinoin (2.4g, 8mmol), p-propyl aminobenzoate (1.72g, 9.6mmol), stirred at room temperature for 15min, then added DCC (2.15g, 10.4mmol), stirred at 30°C for about After 5 hours, the reaction stopped. The above reactions were carried out under the protection of nitrogen and away from light. The above reaction mixture was placed at 0-5°C for about 12 hours, taken out and filtered, and the filtrate was rotary evaporated to obtain a crude product, which was separated by column chromatography (200-300 mesh silica gel, eluent: ethyl acetate:petroleum ether 1:20 ( V / V)), and the resulting product was recrystallized from ethanol to obtain a reaction product (2.9 g). The molecular mass of the reaction product is 461.65, and the proton n...
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