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

HRID 1018841Notes

Reaction equation

HRID 1018841 reaction equation
[NH2:1][CH:2]([CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4].[C:12](#N)[CH3:13]>>[CH:7]1([CH2:6][CH:2]([N:1]2[CH2:13][C:12]3[C:2](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:3]2=[O:4])[C:3]([OH:5])=[O:4])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 2295792-Amino-3-cyclopentylpropanoic acid

Product 1

HCID 184022093-Cyclopentyl-2-(1-oxoisoindolin-2-yl)propanoic acidYield 83%

Procedure

A mixture of 2-Amino-3-cyclopentyl-propionic acid (0.800 g; 5.09 mmol) and phthalic dicarboxaldehyde (0.684 g; 5.10 mmol) in acetonitrile (30 mL) was refluxed for 3 h under nitrogen. The mixture was allowed to cool to room temperature and the solid was filtered off and washed once with cold acetonitrile (5 mL) to give 1.16 g (83%) of 3-Cyclopentyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid as a white solid: EI-HRMS m/e calcd for C16H19NO3 (M+) 273.1365, found 273.1374.

Workup

  1. temperaturewas refluxed for 3 h under nitrogen
  2. filtrationthe solid was filtered off
  3. washwashed once with cold acetonitrile (5 mL)

Sources & evidence

ORD record
ord-cdce0003088d4367ae32c961f5337e2b
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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