L-Glutamine → 2-(4-Nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid

HRID 844220Notes

Reaction equation

HRID 844220 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[N+:11]([C:14]1[CH:24]=[CH:23][CH:22]=[C:16]2[C:17]([O:19][C:20](=O)[C:15]=12)=[O:18])([O-:13])=[O:12]>C(O)(=O)C>[N+:11]([C:14]1[CH:24]=[CH:23][CH:22]=[C:16]2[C:15]=1[C:20](=[O:19])[N:1]([CH:2]([CH2:3][CH2:4][C:5](=[O:7])[NH2:6])[C:8]([OH:10])=[O:9])[C:17]2=[O:18])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 5961L-GlutamineHCID 216313-Nitrophthalic anhydride

Product 1

HCID 155498382-(4-Nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of glutamine (10 mmol) and 3-nitrophthalic anhydride (10 mmol) in 15 ml of acetic acid is heated to reflux. The cooled reaction mixture is concentrated and the residue purified by chromatography to afford 2-(4-nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid.

Workup

  1. temperatureis heated to reflux
  2. customThe cooled reaction mixture
  3. concentrationis concentrated
  4. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-bf66b1f98d1f4d3cb6def6eed68fed3d
Source dataset
uspto-grants-2002_04
Patent number
US06380239B1

Reaction notes

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