Phthalaldehyde → (S)-3-Cyclopentyl-2-(1-oxoisoindolin-2-yl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of benzene-1,2-dicarbaldehyde (1.9 g, 14 mmol) and (S)-2-amino-3-cyclopentyl-propionic acid (2.0 g, 13 mmol) in acetonitrile was heated to reflux for 17 h. The solution was cooled to 4° C. for 3 h during which time a precipitate formed. The mixture was filtered and the solid washed with cold acetonitrile and dried under vacuum to give (S)-3-cyclopentyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid (3.0 g, 86%) as a white solid: LR-ES(+) m/e calcd for C16H19NO3 [M+H]+ 274.15, observed 274.1; 1H NMR (300 MHz, DMSO-d6) δ ppm 0.89-2.29 (m, 11H), 4.23-5.12 (m, 3H), 7.20-7.99 (m, 4H), 13.00 (s, 1H).

Provenance & Evidence