Diethyl Pyrocarbonate → 2-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]prop-2-enamide

関与物質

反応手順

A solution of acid 4B (0.35 g, 1.28 mmol) in THF (25 mL) was added with DEPC (0.25 mL, 1.3 mol eq) and the mixture was stirred at room temperature for 10′. Then [3-[4-(trifluoromethoxy)phenyl]phenyl]methanamine 23B (0.376 g, 1.1 mol eq) and a catalytic amount of TEA were added, then the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, water (40 mL) was added to the residue that is extracted with EtOAc (3×25 mL) and washed with brine (1×40 mL). The separated organic phase was anydrified over Na2SO4, evaporated to dryness and the residue was purified by flash chromatography (1:1 EtOAc:Petroleum ether) to afford a white solid (0.15 g) after recrystallization from ethyl ether. Yield=24%, 1HNMR (DMSO, 200 MHz) δ 1.08 (t, 3H, J=8), 3.37 (q, 2H, J=7.5), 4.44 (d, 2H, J06.1), 5.16 (s, 1H), 6.09 (s, 1H), 7.32 (d, 1H), 7.46 (m, 5H), 7.53 (d, 1H), 7.62 (s, 1H), 7.76 (dd, 2H), 7.86 (m, 2H), 8.78 (t, 1H); [M+1] 522.51 (C25H22F4N2O4S requires 522.12).

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