Aryl alkane acid derivative containing pepper ring and preparation method thereof
An alkyl and compound technology, applied in the field of medicine, can solve the problems of unclear mechanism, low side effects, slow onset of action, etc., and achieve the effects of reducing pharmaceutical activity, small side effects, and low cost
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Embodiment 1
[0047] The preparation of embodiment 1 compound (II)
[0048]
[0049] The preparation of compound (II):
[0050]
[0051] ⑴ Put 2.0g of 3.4-methyleneoxybenzoic acid in an ice-water bath at about 0°C, add 6ml of thionyl chloride dropwise, drop slowly, and finish adding dropwise in about 30 minutes. After that, stir for a while; then, Add 2 to 3 drops of N,N-dimethylformamide as a catalyst, slowly heat to reflux, the whole process is about 1 hour, and reflux for 2 hours.
[0052] (2) Evaporate excess thionyl chloride by a rotary evaporator to obtain a white solid. The solid was dissolved in about 30ml of tetrahydrofuran and set aside.
[0053] (3) Dissolve 1.5g of p-hydroxyphenylethylamine in 30ml of 2.3g of NaOH aqueous solution, and add the solution of (2) dropwise under ice-water bath. The whole process lasts for about 30 minutes, white smoke is generated, and the reaction is stirred overnight.
[0054] (4) The tetrahydrofuran was distilled off by a rotary evaporato...
Embodiment 2
[0058] The preparation of embodiment 2 compound (II)
[0059]
[0060] The preparation of compound (II):
[0061]
[0062] (1) Dissolve 1.0g of 3.4-methyleneoxybenzoic acid, 0.7g of p-hydroxyphenylethylamine and 1.5g of HAUT in 20ml of N,N-dimethylformamide, the solution is clear and transparent, and stir overnight for reaction.
[0063] (2) Add 60ml of water to the reaction solution, extract the aqueous solution with chloroform 3 times, 90ml each time, combine the extracts, use a rotary evaporator to rotate the extract layer to about 80ml, and extract the organic phase with 5% NaOH aqueous solution, 60ml each time, The organic layer was colorless, about 4 times, and the water was combined, and the water was acidified with dilute sulfuric acid, and then filtered to obtain a precipitate. After drying, the product was about 1.44g, and the yield was about 84%.
[0064] (3) Dissolve 0.2g of the product from step (2) in 30ml of acetone, add 0.5g of NaOH fine powder (ground i...
Embodiment 3
[0066] The preparation of embodiment 3 compound (III)
[0067]
[0068] The preparation of compound (III):
[0069]
[0070] ⑴Dissolve 1.0g of 3-(3.4-methyleneoxyphenyl)2-acrylic acid, 0.7g of p-hydroxyphenylethylamine and 1.4g of HAUT in 20ml of N,N-dimethylformamide, and the reaction solution gradually becomes Cloudy, stirred overnight reaction.
[0071] (2) Add 60ml of water to the reaction solution, the reaction solution is clarified, and then extract 3 times with chloroform, 80ml each time, combine the extracts, rotate with a rotary evaporator until about 90ml of chloroform remains, and extract the organic phase with 5% NaOH until the organic phase is colorless, A total of 3 times, 80ml each time, combined the aqueous solution, acidified the aqueous solution with dilute sulfuric acid, filtered to obtain a precipitate, and obtained 1.32g of the product after drying, with a yield of about 82%.
[0072] (3) Dissolve 0.2g of the product of step (2) in 30ml of butanone...
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