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

HRID 844229

Reaction equation

HRID 844229 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[NH2:15][C@H:16]([C:22]([OH:24])=[O:23])[CH2:17][CH2:18][C:19](=[O:21])[NH2:20]>CN(C=O)C>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:5]=1[C:10](=[O:11])[N:15]([CH:16]([CH2:17][CH2:18][C:19](=[O:21])[NH2:20])[C:22]([OH:24])=[O:23])[C:7]2=[O:9])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 5961L-GlutamineHCID 216313-Nitrophthalic anhydride

Product 1

HCID 155498382-(4-Nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acidYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
87.5 °C

Procedure

A mixture of 3-nitrophthalic anhydride (1.5 g, 7.8 mmol) and L-glutamine (1.14 g, 7.8 mmol) in DMF (15 mL) is heated at 85-90° C. for 4 hours. The mixture is concentrated in vacuo and the residue is slurried with water (30 mL). The resulting slurry is filtered and the solid is washed with water (10 mL), dried (60° C., <1 mm Hg) to give 2-(4-nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid (1.82 g, 73%); mp 182-184° C.; 1H NMR (DMSO-d6) δ8.33 (d, J=7.7 Hz, 1H), 8.22 (d, J=7.0 Hz, 1H), 8.11 (t, J=7.8 Hz, 1H), 7.19 (s, 1H), 6.73 (s, 1H), 4.82-4.77 (dd, J=4.6 and 9.8 Hz, 1H), 2.36-2.11 (m, 4H); 13C NMR (DMSO-d6) δ173.21, 170.03, 165.43, 162.75, 144.45, 136.70, 132.98, 128.83, 127.25, 122.52, 51.87, 31.31, 23.87; Anal. Calcd. For C13H11N3O7: C, 48.60; H, 3.45; N, 13.08. Found: C, 48.52; H, 3.28; N, 13.05.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. filtrationThe resulting slurry is filtered
  3. washthe solid is washed with water (10 mL)
  4. customdried (60° C., <1 mm Hg)

Sources & evidence

ORD record
ord-a08c992d0ecd423c89c997531ae1e485
Source dataset
uspto-grants-2002_04
Patent number
US06380239B1

Linked notes

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