Beta-Propiolactone → 3-[3',5'-Dichloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-yloxy]-propionic acid

Participants

Reaction Steps

Treat a solution of 1-cyclohexyl-3-(3,5-dichloro-4′-hydroxy-biphenyl-4-ylmethyl)-pyrrolidin-2-one (55) (0.20 g, 0.47 mmol) in THF (3 mL) with a 1 molar solution of potassium tert-butoxide in THF (0.50 mL, 0.49 mmol) and stir for 5 minutes at room temperature. Add dropwise a solution of beta-propiolactone (0.038 g, 0.527 mmol) in THF (3 mL) and stir the reaction at room temperature for 16 hours under N2. Quench the reaction with 1 N HCl, extract with ethyl acetate and water, dry the organic layer (Na2SO4) and purify by normal phase chromatography (30 to 100% gradient of ethyl acetate in hexanes) to afford 26 mg (11%) of the title compound: LC-MS (ES+) m/z=exact mass calcd for C26H29Cl2NO4 489, found 490 and 492 (M+1 and M+3, 100%).

Provenance & Evidence