Реакция #45331

Уравнение реакции

H2O

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

methyl chloroformate

N,N-diisopropylethylamine

→

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

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   ЭкстракцияThe mixture was extracted with EtOAc (70 mL)
2. 2
   Промывкаthe organic extracts were washed with brine (25 mL)
3. 3
   Сушкаdried over Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеPurification by flash chromatography with 2% to 20% EtOAc/hexanes

Методика

To a solution of {[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]amine (428 mg, 0.81 mmol) and methyl chloroformate (126 μL, 1.39 mmol) in CH2Cl2 (10 mL) was added N,N-diisopropylethylamine (566 μL, 3.25 mmol). The reaction was stirred at room temperature for twenty minutes and then was poured into H2O (25 mL). The mixture was extracted with EtOAc (70 mL), and the organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 2% to 20% EtOAc/hexanes afforded methyl {[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]carbamate. Rf=0.37 (25% EtOAc/hexanes). LCMS=585.3 (M+1)+. 1H NMR (C6D6, 500 MHz, 70° C.) δ 8.03 (s, 1H), 7.78 (s, 1H), 7.64 (s, 1H), 7.37 (s, 1H), 7.33 (d, J=8.0 Hz, 1H), 7.04-7.06 (m, 2H), 6.83 (s, 1H), 6.60 (d, J=8.4 Hz, 1H), 4.37 (bs, 2H), 3.93 (bs, 2H), 3.36 (s, 3H), 3.26 (s, 3H), 2.73 (m, 1H), 1.15 (d, J=6.8 Hz, 6H).

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