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

HRID 2365721Notes

Reaction equation

[C:1]1([CH:9]=O)[C:2]([CH:7]=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:11][C@@H:12]([CH2:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[C:13]([OH:15])=[O:14]>C(#N)C>[CH:17]1([CH2:16][C@H:12]([N:11]2[CH2:9][C:1]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:7]2=[O:8])[C:13]([OH:15])=[O:14])[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

Conditions

Temperature: 4 °C

Procedure

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).

Workup

temperatureto reflux for 17 h
customformed
filtrationThe mixture was filtered
washthe solid washed with cold acetonitrile
customdried under vacuum

Sources & evidence

ORD record: ord-057d7a1df25a4c52a84aa149474008b0
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697705B2

Reaction notes

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