A kind of preparation method of (+)-danshensu and its analog
A technology of danshensu and its synthesis method, which is applied in the field of medicine, can solve the problems of low industrialization value, long reaction steps, asymmetric epoxidation and high price of asymmetric reduction reaction reagents, etc., and achieve low reaction reagents and safe reaction process , does not produce the effect of environmental pollution
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Embodiment 12
[0044] Example 1 2(R), 3-Glycidic acid (Compound 1)
[0045] Add 10.0g (100mmol) of L-serine and 50mL of water into a 250mL three-neck flask, cool to -10°C, add sodium nitrite-hydrobromic acid solution (20.7g of sodium nitrite dissolved in 100mL of 3M hydrobromic acid solution) dropwise, After completion, continue to stir for 12 hours; after the reaction is completed, extract with ethyl acetate (100mL×3), combine the extracts, concentrate to dryness under reduced pressure and dissolve in 100mL ethanol, then add 11.2g KOH under ice bath, and stir for 12h. After the reaction was completed, 500 mL of water was added, and the pH was adjusted to 3 with HCl. A large number of crystals were washed out, filtered with suction, washed with ice water, and dried to obtain 78 g of white crystal compound 1 with a yield of 88.6%.
Embodiment 2
[0046] Example 2 3,4-dibenzyloxy (+)-danshensu
[0047] Add 3,4-dibenzyloxybromobenzene (18.4g, 50mmol) into 500mL of diethyl ether solution, cool to -50°C, add 1M n-butyl lithium solution (50mmol) dropwise, and continue stirring for 0.5 hours ; Then the above reaction solution was added dropwise to the ether solution of compound 1 (50 mmol) at -50°C, and reacted at room temperature for 0.5 h after the dropwise addition. After the reaction was completed, ethyl acetate was extracted three times with water, and the extracts were combined and concentrated to dryness under reduced pressure to obtain 18.8 g of solid. Yield: 99%.
Embodiment 3
[0048] Example 3 3,4-dibenzyloxy (+)-danshensu (2)
[0049] 3,4-dibenzyloxybromobenzene (18.4g, 50mmol) was added to 500mL of diethyl ether solution, metal magnesium (15g, 75mmol) was added under ice-cooling, and then the temperature was slowly raised to reflux for 1h, and the filtrate was obtained by filtration; then The filtrate was added dropwise to the diethyl ether solution of compound 1 (50 mmol) under the condition of stirring in an ice bath, and reacted at room temperature for 0.5 h after the dropwise addition. After the reaction was completed, ethyl acetate was extracted three times with water, and the extracts were combined and concentrated to dryness under reduced pressure to obtain 18.4 g of solid. Yield: 96%.
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