Organic amine ester derivative drug of 2-(alpha hydroxyl amyl) benzoic acid
A hydroxypentyl, benzoic acid technology, applied in the preparation of organic compounds, the preparation of aminohydroxy compounds, organic chemistry and other directions, can solve the problems of high environmental and pH value requirements, increase production costs, reduce production costs, etc. The method is simple, the production cost is low, and the effect of improving the druggability
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Embodiment 1
[0042] Example 1. Synthesis of 2-(1-acetoxypentyl)benzoic acid (compound 4).
[0043] Dissolve 1.24g (6.5mmol) butylphthalide in 10 mL methanol, add 10 mL 2mol L -1 Sodium hydroxide solution, refluxed for 0.5h. Evaporate methanol under reduced pressure, add 10 mL of distilled water to dilute, cool to -5°C, and use 0.6 mol L -1 Acidify with dilute hydrochloric acid to pH 2~3, extract the aqueous layer with ether (50 mL×3), dilute the ether solution with 200 mL of dichloromethane, add 2.7 mL (19.6 mmol) of triethylamine and 0.5 g of 4-dimethylamino Pyridine (DMAP), 1.5mL (19.6 mmol) 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
[0044] Example 2. Synthesis of Compound DB-1.
[0045] 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 column purification, to obtain a white solid, adding absolute ethanol HCl solution to form a salt, adding ether to form a white precipitate, filtering, drying to obtain the hydrochloride product, namely compound DB-1 hydrochloride.
[0046] 1 H NMR (400 MHz, D 2 O) δ 7.88 (dd, J = 7.8, 1.3 Hz, 1H), 7.65 – 7.52(m, 2H), 7.39 (ddd, J = 8.0, 7.0, 1.7 Hz, 1H), 6.30 (dd, J = 8.4, 4.8 Hz,1H), 4.70 – 4.55 (m, 2H), 3.60 (t, J = 5.0 Hz, 2H), 2.94 (s, 6H), 2.04 (s,3H), 1.79 (dddd, J = 18.7, 14.2, 11.1, 5.7 Hz, 2H), 1.38 – 1.21 (m, 4H), 0.79(t, J = 7.1 Hz, 3H).
Embodiment 3
[0047] Example 3. Synthesis of Compound DB-2.
[0048] Weigh 0.5g of 2-(1-acetoxypentyl)benzoic acid, add 50ml of dichloromethane, 0.9g of HATU, 0.8ml of 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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