反应 #45352

反应方程式

H2O

K2CO3

methyl[3-cyano-5-(trifluoromethyl)benzyl]{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

H2O2

→

methyl[3-(aminocarbonyl)-5-(trifluoromethyl)benzyl]{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

溶剂

EtOAc

DMSO

反应条件

后处理

1. 1
   萃取The organic extract
2. 2
   洗涤was washed with brine (10 mL)
3. 3
   干燥dried over Na2SO4
4. 4
   过滤filtered
5. 5
   浓缩concentrated
6. 6
   其他Purification by flash chromatography with 5% to 80% EtOAc/hexanes

实验过程

A solution of methyl[3-cyano-5-(trifluoromethyl)benzyl]{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (35.0 mg, 0.06 mmol) (Example 36) in DMSO (248 μL) was cooled to 0° C. Next, K2CO3 (17.4 mg, 0.05 mmol) was added followed by 30% H2O2 (42.2 μL), and the reaction was slowly warmed to room temperature. After stirring at room temperature for 15 minutes, the mixture was diluted with EtOAc (50 mL) and poured into H2O (15 mL). The organic extract was washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 5% to 80% EtOAc/hexanes afforded methyl[3-(aminocarbonyl)-5-(trifluoromethyl)benzyl]{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate. Rf=0.45 (20% EtOAc/hexanes). LCMS=583.3 (M+1)+. 1H NMR (C6D6, 500 MHz, 70° C.) δ 7.75 (s, 1H), 7.68 (s, 2H), 7.35 (s, 1H), 7.34 (s, 1H), 7.08-7.04 (m, 2H), 6.87 (d, J=2.5 Hz, 1H), 6.62 (d, J=8.5 Hz, 1H), 5.08 (broad singlet, 2H), 4.41 (broad singlet, 2H), 4.07 (broad singlet, 2H), 3.37 (s, 3H), 3.29 (s, 3H), 2.75 (m, 1H), 1.16 (d, J=7.5 Hz, 6H).

来源