Hydrochloric Acid → (S)-3-cyclopentyl-2-(1-oxo-4-trifluoromethyl-1,3-dihydro-isoindol-2-yl)-propionic acid

Participants

Reaction Steps

A solution (S)-3-cyclopentyl-2-(1-oxo-4-trifluoromethyl-1,3-dihydro-isoindol-2-yl)-propionic acid methyl ester (350 mg, 0.98 mmol) in tetrahydrofuran (5 mL) at room temperature was treated with a solution of lithium hydroxide monohydrate (82 mg, 1.96 mmol) in water (5 mL). The reaction mixture was then stirred at room temperature for 1 h. The reaction mixture was then acidified to pH=2 with a 1 N aqueous hydrochloric acid solution and extracted with ethyl acetate (3×20 mL). The combined organic layers were then dried over magnesium sulfate, filtered to remove the drying agent, and the filtrate concentrated in vacuo to afford (S)-3-cyclopentyl-2-(1-oxo-4-trifluoromethyl-1,3-dihydro-isoindol-2-yl)-propionic acid (293 mg, 88%) as a colorless oil: [α]28D=−5.3° (c=0.19, methylene chloride); HR-ES(+) m/e calcd for C17H18NO3F3 [M+H]+ 342.1312, observed 342.1310; 1H NMR (300 MHz, DMSO-d6) δ ppm 13.13 (br. s., 1H), 8.02 (t, J=8.15 Hz, 2H), 7.68-7.85 (m, 1H), 4.82 (dd, J=4.23, 11.17 Hz, 1H), 4.69 (s, 2H), 1.02-2.20 (m, 11H).

Provenance & Evidence