Acetonitrile → 3-Cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid

HRID 1018848Notes

Reaction equation

HRID 1018848 reaction equation
[NH2:1][CH:2]([CH2:6][CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4].[C:14](#N)[CH3:15]>>[CH:7]1([CH2:6][CH:2]([N:1]2[CH2:15][C:14]3[C:2](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:3]2=[O:4])[C:3]([OH:5])=[O:4])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 221843862-Amino-3-cycloheptylpropanoic acid

Product 1

HCID 184021683-Cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acidYield 82%

Procedure

A solution of phthalic dicarboxaldehyde (248 mg; 1.80 mmol) and 2-Amino-3-cycloheptyl-propionic acid (318 mg; 1.72 mmol) in acetonitrile was heated to reflux for 18 h. The mixture was then allowed to cool to room temperature and the mixture stored in the refrigerator for 3 h. The solid was filtered off, rinsed with cold acetonitrile and air dried to give 424 mg (82%) of 3-Cycloheptyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid as a beige solid: EI-HRMS m/e calcd for C18H23NO3 (M+) 301.1678, found 301.1668.

Workup

  1. temperatureto reflux for 18 h
  2. filtrationThe solid was filtered off
  3. washrinsed with cold acetonitrile and air
  4. customdried

Sources & evidence

ORD record
ord-00d19ad5eb2041dfaabe8e1cb7076b01
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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