Method for synthesizing monobenzoyl quinate compound
A technology of benzoylquinic acid and benzoylquinic acid, which is applied in the field of synthesizing monosubstituted benzoylquinic acid compounds, can solve the problems of low synthesis yield, achieve mild reaction conditions and simple post-treatment , the effect of simple operation
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Embodiment 1
[0026] Example 1 : Synthesis of compound (1)
[0027] Add 1.2 mmoles of 3,4,5-triacetoxybenzoic acid, 2 mmoles of dicyclohexylcarbodiimide, and 20 ml of anhydrous dichloromethane into the reaction flask, stir at room temperature for 20 minutes, and white turbidity appears Finally, add 1 mmol 3,4-di-oxo-acetonylidene quinic acid, 0.2 mmol 4-dimethylaminopyridine (DMAP), the whole solution was reacted at room temperature for 12 hours, and the insoluble matter was removed by suction filtration, and then dripped Add 5 milliliters of 1N hydrochloric acid, react at room temperature for 3 days, detect that the ratio of product and raw material does not change any more by thin layer chromatography TLC, add table salt to saturation in the reaction system, extract with chloroform (20 milliliters * 4), combine chloroform The layer was washed with a large amount of water, washed with saturated brine, and dried over anhydrous sodium sulfate. With reversed phase column RP-C 18 (60% metha...
Embodiment 2
[0028] Example 2 : Synthesis of compound (1)
[0029] Add 1.2 mmoles of 3,4,5-triacetoxybenzoic acid, 2 mmoles of methylisobutylcarbodiimide, and 20 ml of anhydrous dichloromethane into the reaction flask, stir at room temperature for 20 minutes, and After the white turbidity, add 1 mmol 3,4-di-oxo-acetonylidene quinic acid, 0.2 mmol 4-dimethylaminopyridine (DMAP), the whole solution was reacted at room temperature for 24 hours, and the insoluble matter was removed by suction filtration. Add 5 milliliters of 1N hydrochloric acid dropwise again, and react at room temperature for 62 hours. It is detected by thin-layer chromatography TLC that the ratio of product and raw material does not change any more. Add salt to the reaction system for saturation, and extract with chloroform (20 milliliters × 4). The combined chloroform layers were washed with a large amount of water, washed with saturated brine, and dried over anhydrous sodium sulfate. With reversed phase column RP-C 18...
Embodiment 3
[0030] Example 3 : Synthesis of compound (1)
[0031] Add 1.2 mmoles of 3,4,5-triacetoxybenzoic acid, 2 mmoles of dicyclohexylcarbodiimide, and 20 ml of anhydrous dichloromethane into the reaction flask, stir at room temperature for 20 minutes, and white turbidity appears Finally, add 1 mmol 3,4-di-oxo-acetonylidene quinic acid, 0.2 mmol 4-pyrrolidinylpyridine (PPY), and the whole solution was reacted at room temperature for 18 hours, and the insoluble matter was removed by suction filtration, and then dripped Add 5 milliliters of 1N hydrochloric acid, react at room temperature for 3 days, detect that the ratio of product and raw material does not change any more by thin layer chromatography TLC, add table salt to saturation in the reaction system, extract with chloroform (20 milliliters * 4), combine chloroform The layer was washed with a large amount of water, washed with saturated brine, and dried over anhydrous sodium sulfate. With reversed phase column RP-C 18 (60% me...
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