Diethyl Ether → HCID 67520924, compound

Participants

Reaction Conditions

Reaction Steps

To a magnetically stirred mixture of (S)-3-Cyclopentyl-2-(3-oxo-3,3a-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-propionic acid methyl ester (0.64 g, 1.88 mmol) in THF (9 mL) and water (3 mL) was added lithium hydroxide (0.102 g, 2.44 mmol). After addition was complete the mixture was stirred at 25° C. for 2 hours. The reaction mixture was poured into water and ether and the layers separated. The aqueous layer was made acidic with 2N HCl and extracted with three portions of ethyl acetate. The combined ethyl acetate fractions were washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to afford (S)-3-Cyclopentyl-2-(3-oxo-3,9-dihydro-1H-chromeno[2,3-c]pyrrol-2-yl)-propionic acid as a white solid, 500 mg (81% yield). ESI-LRMS m/e calcd for C19H21NO4 [M+] 327, found 328 [M+H+]. (Note: The double bond isomerizes during the course of the reaction based on NMR spectrum)

Provenance & Evidence