Gamma-Aminobutyric Acid → 4-Phthalimidobutyric acid

HRID 1604217Notes

Reaction equation

HRID 1604217 reaction equation
[C:1]([N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])(OCC)=O.NC[CH2:19][CH2:20][C:21]([OH:23])=[O:22].C(=O)([O-])[O-].[Na+].[Na+]>O>[C:7]1(=[O:16])[N:6]([CH2:1][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]12

Participants

5

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 10340Sodium CarbonateHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 184114-Phthalimidobutyric acidYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Carboethoxyphthalimide (10.96 g) was added on one portion to a vigorously stirred solution of 4-aminobutanoic acid (5.16 g) and sodium carbonate (5.35 g) in water (150 ml) at RT. The mixture was stirred until essentially all the solid material had dissolved (30 min), then it was filtered. The filtrate was acidified to pH1 with 6N aqueous hydrochloric acid (ca. 22 ml) and the white precipitate was collected by filtration and washed thoroughly with water (150 ml). The solid was dried in air, then in vacuo to give the title compound as a colourless solid (7.35 g).

Workup

  1. dissolutionhad dissolved (30 min)
  2. filtrationit was filtered
  3. filtrationthe white precipitate was collected by filtration
  4. washwashed thoroughly with water (150 ml)
  5. customThe solid was dried in air

Sources & evidence

ORD record
ord-283f5d3105664bd682b66daf44925f51
Source dataset
uspto-grants-1999_11
Patent number
US05994312

Reaction notes

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