Peptoid compounds containing tertiary leucine and preparation method and application of peptoid compounds containing tertiary leucine
A technology for tert-leucine and compounds, which is applied in the field of peptoid compounds containing tert-leucine and its preparation and application, can solve problems such as adverse reactions and drug resistance, and achieve good spatial matching effects
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[0032] see figure 1 , the preparation method of the peptoid compound containing tert-leucine of above-mentioned structure, comprises the following steps:
[0033] 1) Acylation of 5-bromo-2-aminopyridine with the corresponding acid chloride compound to prepare acylated 5-bromo-2-aminopyridine;
[0034] The specific process of the described step 1) is: dissolving 5-bromo-2-aminopyridine in anhydrous dichloromethane, adding triethylamine, and slowly adding the corresponding acid chloride compound dropwise to the above solution under ice-bath conditions After the dropwise addition was completed, the ice bath was removed and the reaction was carried out at room temperature for 12 hours. After the reaction, add dichloromethane to dilute, wash with water, wash with saturated sodium bicarbonate, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, distill under reduced pressure, and separate by column chromatography to obtain a white solid, which is the acylated 5-...
Embodiment 1
[0048] A peptoid compound containing tert-leucine, R is , the preparation method is as follows:
[0049] 1) Synthesis of N-(5-bromopyridin-2-yl)acetamide: 5-bromo-2-aminopyridine (5.19 g, 30 mmol) was dissolved in 100 ml of anhydrous dichloromethane, and 20 ml of triethylamine was added. Under the condition of ice bath, acetyl chloride (2.54ml) was slowly added dropwise to the above solution. After the dropwise addition was completed, the ice bath was removed, and the mixture was raised to room temperature to react overnight (reaction 12h). After the reaction was finished, dichloromethane was added for dilution, washed with water (30ml×3), saturated NaHCO 3 Solution washing (30ml×3), saturated NaCl washing (30ml), organic phase anhydrous NaCl 2 SO 4 dry. Column chromatography separated 5.65 g of white solid with a yield of 88%. Mp 78-81℃; EI-MS(m / z):214[M] + .
[0050] 2) Synthesis of 4-(6-(acetylamino)pyridin-3-yl)benzoic acid: N-(5-bromopyridin-2-yl)acetamide (4.30g,...
Embodiment 2
[0056] A peptoid compound containing tert-leucine, R is , the preparation method is as follows:
[0057] 1) in N 2 Under protection, add thionyl chloride (36ml, 494mmol) dropwise to 5-bromonicotinic acid (5.00g, 24.7mmol). After the dropwise addition, heat to reflux for 2-3h until the solution is clear, and spin off the chloride under reduced pressure. Sulfoxide, a light yellow solid was obtained. The solid was dissolved in 30ml of anhydrous dichloromethane, and the reactive intermediate solution was slowly added dropwise to a solution of cyclopropylamine (3.77ml) in dichloromethane (30ml) in an ice bath. After the dropwise addition, it was raised to room temperature and reacted overnight. After the reaction, add 2mol / L K to the reaction system 2 CO 3 Solution 20ml. Separate the liquid to take the dichloromethane phase, extract the aqueous phase with dichloromethane (15ml × 3), combine the organic phases, anhydrous Na 2 SO 4 dry. Column chromatography separation and ...
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