Gamma-Aminobutyric Acid → 4-Phthalimidobutyric acid

HRID 567686Notes

Reaction equation

HRID 567686 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 in 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 6 N 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-0639948401f84b148d90b47165e72932
Source dataset
uspto-grants-2001_01
Patent number
US06180611B2

Reaction notes

Loading…