반응 #1135909

반응 방정식

acetic acid

tetrahydrofurane

sodium hydroxide

4,4-dimethyl-3-((3-((3-(trifluoromethyl)phenyl)ethynyl) imidazo[1,2-a]pyridin-2-yl)methylthio)dihydrofuran-2(3H)-one

→

4-hydroxy-3,3-dimethyl-2-((3-((3-(trifluoromethyl)phenyl)-ethynyl)imidazo[1,2-a]pyridin-2-yl)methylthio) butanoic acid

용매

water

methanol

반응 조건

후처리

1. 1
   여과was then filtered
2. 2
   세척washed with water

실험 절차

130 mg (0.303 mmol) of 4,4-dimethyl-3-((3-((3-(trifluoromethyl)phenyl)ethynyl) imidazo[1,2-a]pyridin-2-yl)methylthio)dihydrofuran-2(3H)-one were dissolved in 2 ml of methanol and 2 ml of tetrahydrofurane followed by the addition of 0.334 ml (0.334 mmol) of a 1N sodium hydroxide aqueous solution. The solution was stirred for 16 h. It was acidified down to an acid pH with acetic acid, and diluted with water until precipitation of a solid, which was then filtered and washed with water. 115 mg of 4-hydroxy-3,3-dimethyl-2-((3-((3-(trifluoromethyl)phenyl)-ethynyl)imidazo[1,2-a]pyridin-2-yl)methylthio) butanoic acid were obtained as a pale brown solid. LC-MS: m/z=447 (MH+) UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 12.69 (s, 1H), 8.77 (d, J=6.7 Hz, 1H), 8.11 (s, 1H), 7.97 (d, J=7.5 Hz, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.70 (t, J=8.2 Hz, 2H), 7.54-7.41 (m, 1H), 7.16 (t, J=6.6 Hz, 1H), 4.81 (d, J=12.3 Hz, 1H), 4.70 (sl, 1H), 4.58 (d, J=12.3 Hz, 1H), 3.92 (s, 1H), 3.40 (s, 1H), 3.10 (d, J=10.4 Hz, 1H), 0.86 (s, 3H), 0.82 (s, 3H)

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