反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
Methyl{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-(methylthio)-5-(trifluoromethyl)benzyl]carbamate (18.0 mg, 0.031 mmol) (Example 129) in CH2Cl2 (1 mL) was cooled to 0° C. Next, m-CPBA (17.3 mg, 0.078 mmol) was added. The reaction was stirred at 0° C. for fifteen minutes and then was poured into NaHSO3 (10 mL). The mixture was extracted with EtOAc (50 mL), and the organic extracts were washed with water (10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 50% EtOAc/hexanes afforded methyl{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-(methylsulfonyl)-5-(trifluoromethyl)benzyl]carbamate. Rf=0.61 (50% EtOAc/hexanes). LCMS=618.2 (M+1)+.1H NMR (C6D6, 500 MHz, 70° C.) δ 8.01 (s, 1H), 7.73 (s, 1H), 7.59 (broad singlet, 1H), 7.44 (broad singlet, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.06 (s, 1H), 7.05 (s, 1H), 6.87 (d, J=2.5 Hz, 1H), 6.63 (d, J=8.5 Hz, 1H), 4.39 (broad singlet, 2H), 3.96 (broad singlet, 2H), 3.36 (s, 3H), 3.31 (s, 3H), 2.75 (m, 1H), 2.20 (s, 3H), 1.16 (d, J=7.0 Hz, 6H).
WORKUP
后处理
- extractionThe mixture was extracted with EtOAc (50 mL)
- washthe organic extracts were washed with water (10 mL), brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customPurification by flash chromatography with 50% EtOAc/hexanes