반응 #47457

반응 방정식

water

2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(1-fluoro-cyclopentyl)-propionic acid ethyl ester

lithium hydroxide monohydrate

→

2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(1-fluoro-cyclopentyl)-propionic acid

수율 88.0%

용매

tetrahydrofuran water

반응 조건

후처리

1. 1
   세척washed with diethyl ether
2. 2
   추출extracted with ethyl acetate (2×30 mL)
3. 3
   건조The combined ethyl acetate layers were dried over magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated

실험 절차

To a solution of 2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(1-fluoro-cyclopentyl)-propionic acid ethyl ester (0.440 g, 1.11 mol) in tetrahydrofuran:water (1:1, 10 mL) was added lithium hydroxide monohydrate (0.140 g 3.34 mmol). The mixture was stirred at room temperature for 2 h. The reaction mixture was poured into water and washed with diethyl ether and the diethyl ether layer discarded. The aqueous phase was acidified with 1N aqueous hydrochloric acid (pH <2), and extracted with ethyl acetate (2×30 mL). The combined ethyl acetate layers were dried over magnesium sulfate, filtered and concentrated to afford 2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(1-fluoro-cyclopentyl)-propionic acid, (0.358 g, 88%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.64 (br. s., 8H), 2.34 (dd, J=22.6, 6.9 Hz, 2H), 4.23 (d, J=18.4 Hz, 1H), 4.31 (d, J=18.4 Hz, 1H), 4.84 (t, J=6.9 Hz, 1H), 5.05 (s, 1H), 7.26-7.55 (m, 3H), 13.05 (br. s., 1H).

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