Method for synthesizing important ezetimibe intermediate-(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1, 3-oxazolidine-2-ketone
A technology of oxacyclopentane and ezetimibe, which is applied to an important intermediate of ezetimibe (4S)-3-[(5S)-5-(4-fluorophenyl)-5- The field of synthesis of hydroxyvaleryl]-4-phenyl-1,3-oxazacyclopentan-2-one can solve the problems of large environmental pollution, high cost and high cost
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example 1
[0022] Under nitrogen, add 20 grams of p-fluorobenzoyl butyric acid, 10 grams of S-4-phenyl-2-oxazolidinone, 20.1 grams of EDCI, 1.6 grams of DMAP, and 100ml of dichloromethane into a 250ml single-necked flask at room temperature. After stirring for 24 hours, TLC monitored the reaction to be complete. Add 100ml of 1N hydrochloric acid, separate the liquids, wash and dry with water, and concentrate to obtain 19 grams of off-white solid. Recrystallize with isopropanol to obtain 16 grams of white solid, which is the compound. Melting point: 91.6-92.4°C, purity 99.9% (HPLC).
[0023] MS(ESI): 356(M+H), 1 H-NMR(CDCl 3 -d1): δ-2.0~2.1(m,2H), 2.94~2.99(m,2H), 3.03~3.03(m,2H), 4.27~4.31(m,1H), 4.67~4.73(m,1H) , 5.41 ~ 5.45 (m, 1H), 7.01 ~ 7.13 (m, 2H), 7.29 ~ 7.39 (m, 5H), 7.90 ~ 7.95 (m, 2H).
example 2
[0025] Under nitrogen, add 19.5g (55mmol) of compound I and 200ml of dichloromethane to a three-necked flask, cool to -20°C, dropwise add 32ml of homemade isopinylchloroborane (60% n-hexane solution, concentration 1.7mol) / L), control the internal temperature not to be higher than -20°C, stir at -20°C for 1 hour after the dropwise addition is completed, then stir at 0°C for 1 hour, and naturally rise to room temperature and stir until the conversion is complete. After quenching by adding a small amount of potassium carbonate solution dropwise, 200 ml of potassium carbonate solution was added to separate the layers, the organic layer was dried and concentrated to obtain a colorless oil, and the compound II was obtained by column chromatography with a mixture of n-hexane and ethyl acetate.
[0026] MS(ESI): 380(M+Na + ), 1 H-NMR (CDCl3-d1): δ-1.60~1.82(m,4H), 2.96~3.02(m,2H), 4.26~4.30(m,1H), 4.61~4.65(m,1H), 4.66~4.71 (m, 1H), 5.40 to 5.42 (m, 1H), 6.98 to 7.01 (m, 2H), 7.25 to 7....
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