A kind of preparation method of antibacterial compound
A compound and catalyst technology, applied in the field of medicine and chemical industry
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Embodiment 1
[0064] Example 1 (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)3-fluorophenyl)-5-hydroxymethyloxazolidine-2 - the preparation of ketone (formula V compound)
[0065] Add DMSO (100ml), (5R)-3-(4-bromo-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one (10g, 34.5mmol) and diboronic acid to a 250ml reaction bottle Naol ester (17.52g, 69mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (1.41g, 1.73mmol) and potassium acetate (13.5g , 138mmol), under the protection of nitrogen, the temperature was raised to 80°C, and the reaction was carried out for 14 hours. Stop heating, lower to room temperature, extract with water / ethyl acetate 3 times, combine organic layers, wash 3 times with saturated brine, dry over anhydrous sodium sulfate, and concentrate by suction filtration.
[0066] Add the concentrated product of the above steps to a 250ml reaction flask, add 1,4-dioxane (100ml), 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine (8.28 g, 34.5mmol), ...
Embodiment 2
[0070] Example 2 (R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidine Base] the preparation of bis(benzyl ester) of methyl phosphate (compound of formula VII)
[0071] Add dichloromethane (100ml), 1H-tetrazolium (5.97g, 85.2mmol) and compound of formula V (10.5g, 28.4mmol) into a 500ml three-necked flask, and add diisopropylaminophosphorous acid dropwise under temperature control below 30°C Dibenzyl ester (19.6g, 56.8mmol) was reacted at 25-30°C for 30min. Cool down to 0-10°C, add 85% m-chloroperoxybenzoic acid (8.08g, 39.8mmol), and react at 5-10°C for 30min.
[0072] The reaction solution was sequentially washed with saturated NaHCO 3 Washed twice, washed once with saturated NaCl, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain 14.89 g of the title compound with a yield of 83.1% and a purity of 99.62% by HPLC (area normalization method).
[0073] 1 H NMR (500MHz, DMSO-d6): δ8.93...
Embodiment 3
[0076] The preparation of embodiment 3 tedizolid phosphate (formula I compound)
[0077] Add dichloromethane (50ml), trifluoroacetic acid (55ml), and compound of formula VII (12g) into a 500ml reaction flask, stir and dissolve at 40-45°C, and react for 16 hours. Concentrate under reduced pressure at 40-45°C until no liquid flows out, add 80ml of absolute ethanol and stir for 3 hours, filter, wash the filter cake with 18ml of absolute ethanol, and vacuum-dry the filter cake at 40-45°C for 16 hours to obtain 8.14g of the title compound. The yield was 95.0%, and the purity detected by HPLC was 99.23% (area normalization method).
[0078] 1 H NMR (500MHz, DMSO-d6): δ8.9367(s,1H),8.2052(m,2H),7.72(m,2H),7.5162(m,1H),4.99(m,1H),4.4961(s ,3H), 4.2546(t,1H), 4.1714(m,1H), 4.1035(m,1H), 3.9521(m,1H).
[0079] 13 C NMR(125MHz,DMSO-d6):δ163.854,159.2905,153.925,149.382,145.069,140.286,137.083,131.558,130.87,122.044,118.764,114.079,105.509,71.467,65.457,45.833,39.549。
[0080] ESI-MS...
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