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

HRID 1018853Notes

Reaction equation

HRID 1018853 reaction equation
[NH2:1][CH:2]([CH2:6][CH:7]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4].[C:15](#N)[CH3:16]>>[CH:7]1([CH2:6][CH:2]([N:1]2[CH2:16][C:15]3[C:2](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:3]2=[O:4])[C:3]([OH:5])=[O:4])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 184021902-Amino-3-cyclooctylpropanoic acid

Product 1

HCID 184021673-Cyclooctyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acidYield 62%

Procedure

A solution of phthalic dicarboxaldehyde (349 mg; 2.60 mmol) and 2-Amino-3-cyclooctyl-propionic acid (500 mg; 2.51 mmol) in acetonitrile (20 mL) was heated to reflux for 3 h. The mixture was then hot filtered to remove insoluble material and then allowed to cool to room temperature and then further cooled to 0° C. The solid was filtered off, rinsed with cold acetonitrile and air dried to give 480 mg (62%) of 3-Cyclooctyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic acid as a white solid: EI-HRMS m/e calcd for C19H25NO3 (M+) 315.1834, found 315.1840.

Workup

  1. temperatureto reflux for 3 h
  2. filtrationThe mixture was then hot filtered
  3. customto remove insoluble material
  4. temperaturefurther cooled to 0° C
  5. filtrationThe solid was filtered off
  6. washrinsed with cold acetonitrile and air
  7. customdried

Sources & evidence

ORD record
ord-e7d4cfa71caa4bc0be13f101bf913159
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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