L-Glutamine → N-Phthaloyl-L-glutamine

HRID 1417364Notes

Reaction equation

HRID 1417364 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32])(OCC)=O>O>[CH:29]1[CH:28]=[C:25]2[C:26]([N:1]([C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([NH2:6])=[O:7])[C:23](=[O:32])[C:24]2=[CH:31][CH:30]=1)=[O:27]

Participants

5

Reactant 3

HCID 5961L-GlutamineHCID 10340Sodium CarbonateHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 259136N-Phthaloyl-L-glutamineYield 59.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of L-glutamine (43.8 g, 300 mmoL) and sodium carbonate (33.4 g, 315 mmoL) in 750 mL of water is rapidly added N-carbethoxyphthalimide [65.8 (97% pure, 67.8 g), 300 mmoL] as a solid. After 1 hour, the reaction mixture is filtered to remove unreacted N-carbethoxyphthalimide. The pH of the stirred filtrate is adjusted to 3-4 with 4N hydrochloric acid. The mixture is then seeded with N-phthaloyl-L-glutamine and the pH adjusted to 1-2 with 4N hydrochloric acid. The resulting slurry is stirred for 1 hour. The slurry is filtered and the solid washed with copious amounts of water. The solid is air-dried and then dried in vacuo (60° C., <1 mm) overnight to afford 49.07 g (59%) of N-phthaloyl-L-glutamine, which can be alternatively named as 2-phthalimidoglutaramic acid, as a white powder.

Workup

  1. filtrationthe reaction mixture is filtered
  2. customto remove unreacted N-carbethoxyphthalimide
  3. filtrationThe slurry is filtered
  4. washthe solid washed with copious amounts of water
  5. customThe solid is air-dried
  6. customdried in vacuo (60° C., <1 mm) overnight

Sources & evidence

ORD record
ord-7bf0dd97f62f4944970dd3f0659d7bce
Source dataset
uspto-grants-1999_03
Patent number
US05877200

Reaction notes

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