An organic amine ester derivative drug of 2-(α-hydroxypentyl)benzoic acid
A technology of hydroxypentyl and benzoic acid, which is applied in the preparation of organic compounds, the preparation of aminohydroxyl compounds, and drug combinations, etc., which can solve the problems of high environmental and pH requirements, reduce production costs, increase production costs, etc., and achieve connection The method is simple, the druggability is improved, and the production cost is low
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Embodiment 1
[0043] Example 1. Synthesis of 2-(1-acetoxypentyl)benzoic acid (Compound 4).
[0044] Dissolve 1.24g (6.5mmol) butylphthalide in 10mL methanol, add 10mL 2mol·L -1 Sodium hydroxide solution, refluxed for 0.5h. Evaporate methanol under reduced pressure, add 10mL distilled water to dilute, cool to -5°C, and use 0.6mol L -1 Acidify with dilute hydrochloric acid to pH 2~3, extract the aqueous layer with ether (50mL×3), dilute the ether solution with 200mL dichloromethane, add 2.7mL (19.6mmol) triethylamine, 0.5g 4-dimethylaminopyridine (DMAP), 1.5mL (19.6mmol) acetyl chloride was added dropwise at -5°C, and the reaction was stirred at -5°C for 5h after the drop was completed. Add 10 mL of water, stir at room temperature for 0.5 h, separate the organic layer, and dry over anhydrous sodium sulfate. Filtrate and concentrate to obtain a waxy solid, and recrystallize from n-hexane to obtain white needle-like crystals.
Embodiment 2
[0045] Example 2. Synthesis of compound DB-1.
[0046] Weigh 0.5g of 2-(1-acetoxypentyl)benzoic acid, add 50ml of dichloromethane, 0.9g of HATU, 0.6ml of N,N-dimethylethanolamine, stir and react overnight, extract with water three times, dichloromethane / Methanol = 80:1 was purified by column to obtain a white solid, which was formed by adding absolute ethanol HCl to form a salt, and diethyl ether was added to form a white precipitate, which was filtered and dried to obtain the hydrochloride product, namely compound DB-1 hydrochloride.
[0047] 1 H NMR (400MHz,D 2 O)δ7.88(dd,J=7.8,1.3Hz,1H),7.65–7.52(m,2H),7.39 (ddd,J=8.0,7.0,1.7Hz,1H),6.30(dd,J=8.4 ,4.8Hz,1H),4.70–4.55(m,2H),3.60(t,J=5.0Hz,2H),2.94(s,6H),2.04(s,3H),1.79(dddd,J=18.7, 14.2, 11.1, 5.7Hz, 2H), 1.38–1.21 (m, 4H), 0.79 (t, J = 7.1Hz, 3H).
Embodiment 3
[0048] Example 3. Synthesis of compound DB-2.
[0049] Weigh 0.5g 2-(1-acetoxypentyl)benzoic acid, add 50ml dichloromethane, 0.9g HATU, 0.8ml 1-(2-hydroxyethyl)piperidine, stir and react overnight, extract with water three times, two Chloromethane / methanol=80:1 column purification, to obtain a white solid, add absolute ethanol HCl solution to form a salt, add ether to form a white precipitate, filter, dry, and obtain the hydrochloride product, namely compound DB-2 hydrochloride .
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