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MK-2866合成路线(英文版)

发布者:武汉德美凯生物科技有限公司  发布时间:2017-11-16  阅读:512次
MK-2866合成路线(英文版)
 Eswaraka, Jeetendra, US2011/172302, A1, (2011) A mixture of bromoamide ((2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide, 50 g, 0.14 mol), anhydrous K2CO3 (59.04 g, 0.43 mol), 4-cyanophenol (25.44 g, 0.21 mol) in 50 0 mL of 2-propanol was heated to reflux for 3 h and then concentrated under reduced pressure to give a solid.The resulting residue was treated with 500 mL of H2O and then extracted with EtOAc (2*300 m L).The combined EtOAc extracts were washed with 10percent NaOH (4*200 mL) and brine.The organic layer was dried over MgSO4 and then concentrated under reduced pressure to give an oil which was treated with 300 mL of ethanol and an activated carbon.The reaction mixture was heated to reflux for 1 h and then the hot mixture was filtered through Celite.The filtrate was concentrated under reduced press ure to give an oil.This oil was purified by column chromatography using CH2Cl2/EtOAc (80:20) to give an oil which was crystallized from CH2Cl2/hexane to give 33.2 g (59.9percent) of (S)-N-(4-cyano-3-( trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide as a colorless solid (a cotton type).1H NMR (CDCl3/TMS) delta 1.63 (s, 3H, CH3), 3.35 (s, 1H2OH), 4.07 (d, J=9.04 Hz, 1H, CH), 4.51 (d, J=9.04 Hz, 1H, CH), 6.97-6.99 (m, 2H, ArH), 7.57-7.60 (m, 2H, ArH), 7.81 (d, J=8.55 Hz, 1H, ArH), 7.97 (dd, J=1.95, 8.55 Hz, 1H, ArH), 8.12 (d, J=1.95 Hz, 1H, ArH), 9.13 (bs, 1H, NH).Calculat ed Mass: 389.10, [M-H]- 388.1. Mp: 92-94 C.
 

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