Reaktion #45357

Reaktionsgleichung

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

m-CPBA

NaHSO3

→

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

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with EtOAc (50 mL)
2. 2
   Waschenthe organic extracts were washed with water (10 mL), brine (10 mL)
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification by flash chromatography with 50% EtOAc/hexanes

Vorschrift

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=7.0Hz, 6H).

Quelle