Fibric acid compounds and medical uses thereof
A technology of compounds and hydrates, applied in the field of medicine, can solve problems such as threats to health and life safety
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Embodiment 1
[0402] Example 1: Preparation of 5-(4-chloro-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid (BJMU-1)
[0403]
[0404] Step 1: Preparation of isobutyl 5-(4-chloro-2,5-dimethylphenoxy)-2,2-dimethylpentanoate (Int 1)
[0405] Compound 1-1 (4-chloro-2,5-dimethylphenol) (780mg, 5.0mmol), 5-chloro-2,2-dimethylvaleric acid isobutyl ester (1144mg, 5.2mmol), TBAI (36.9mg, 0.1mmol), potassium carbonate (1380mg, 10.0mmol) were dissolved in DMF (30mL), stirred overnight at 90 degrees Celsius, TLC monitored the trend of continuous conversion, the reaction solution was poured into water, separated, and the aqueous phase After extraction with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated, and the crude product was separated by silica gel column chromatography to obtain compound 1-2 (1.5 g), with a yield of 88%.
[0406] The second step: the preparation of 5-(4-chloro-2,5-dimethylphenoxy)-2,2-dimethylpent...
Embodiment 2
[0409] Example 2: Preparation of 5-(4-bromo-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid (BJMU-2)
[0410]
[0411] In the first step in Example 2, compound 2-1 was used to replace the compound 1-1 in the first step in Example 1. The compound BJMU-2 was synthesized by the similar method described in the first step to the second step of Example 1, and the two-step yield was 66%.
[0412] 1 H NMR (400MHz, Chloroform-d) δ7.25(s,1H),6.64(s,1H),3.90(t,J=5.9Hz,2H),2.33(s,3H),2.15(s,3H) ,1.91–1.58(m,4H),1.25(s,6H). 13 C NMR (101MHz, CDCl3) δ184.38, 156.20, 135.57, 133.65, 126.29, 114.58, 113.47, 68.23, 41.94, 36.78, 25.04, 24.98, 22.87, 15.44
Embodiment 3
[0413] Example 3: Preparation of 5-(4-fluoro-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid (BJMU-3)
[0414]
[0415] In the first step in Example 3, compound 3-1 was used to replace the compound 1-1 in the first step in Example 1. The compound BJMU-3 was synthesized by the similar method described in the first step to the second step of Example 1, and the two-step yield was 78%.
[0416] 1 H NMR (400MHz, CDCl3) δ6.78 (d, J = 9.8Hz, 1H), δ6.56 (d, J = 7.0 Hz, 1H), δ3.89 (t, J = 6.0Hz, 2H), δ2 .22(s,3H),δ2.17(s,3H),δ1.85–1.69 (m,4H),δ1.25(s,6H). 13 C NMR (101MHz, CDCl3) δ184.76, 155.12 (d, J = 236.3Hz), 152.72 (d, J = 2.15), 125.60 (d, J = 7.57), 121.61 (J = 18.4), 116.82 (d, J = 23.74), 113.78 (d, J=5.43), 68.69, 41.94, 36.81, 25.12, 24.94, 22.83, 15.41. 19 F NMR (376MHz, CDCl3), δ-129.00 (s, 1F)
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