Lithium hydroxide, monohydrate → HCID 67191193, compound

Participants

Reaction Conditions

Reaction Steps

2-(3-chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-furan-2(R)-yl)-propionic acid methyl ester (180 mg, 0.52 mmol) was dissolved in ethanol (5 mL) and treated with a solution of lithium hydroxide monohydrate (54 mg, 1.3 mmol) in water (1 mL) at 25° C. It was stirred at 25° C. until the starting material was all consumed by TLC. The reaction was then concentrated in vacuo to remove the ethanol. The remaining aqueous layer was then acidified to pH=2 with an aqueous 1N hydrochloric acid solution. This was then extracted with ethyl acetate (3×20 mL), the organic layers combined and dried over magnesium sulfate, filtered and concentrated in vacuo to afford 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-furan-2(R)-yl)-propionic acid (168 mg, 98%) as a reaction of two diastereomers as a white foam: ES-HRMS m/e calcd for C14H17O5SCl (M+H)+ 333.0558, observed 333.0553; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.35-1.49 (m, 1H, CH of CH2), 1.66-1.99 (m, 4H, 4×CH of CH2), 2.06-2.23 (m, 1H, CH of CH2), 3.34, 3.35 (2×s, 3H, SO2CH3), 3.42-3.85 (m, 4H, OCH2 and OCH and ArCH), 7.54 (2×dd, Jo=8.1 Hz, Jm=1.7 Hz, 1H, Ar), 7.66 (2×d, Jm=1.7 Hz, 1H, Ar), 7.99 (2×d, Jo=8.1 Hz, 1H, Ar), 12.69 (brs, 1H, CO2H).

Provenance & Evidence