4-(butylamino)-4-oxobutanoic acid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: n-Butylamine (9.05 g, 0.1225 mole) was dissolved in Et2O (30 ml). Succinic anhydride (5 g, finely powdered) was added portionwise. After addition was complete, the heterogeneous mixture was stirred 1 hour at room temperature. The reaction mixture was then poured into 10% NaOH in H2O (10 ml) and Et2O (30 ml). The layers were separated and the ether layer was extracted with additional 10% NaOH (10 ml). The combined aqueous layers were washed with ether (30 ml) and acidified with concentrated HCl to give a layer of oil above the water layer. This was extracted with Et2O (50 ml×2). The ether extracts were washed with saturated NaCl solution (3×30 ml) and dried (MgSO4). The solvent was removed in vacuo to give a white solid (7.5 g) which was recrystallized from benzene to give title acid as needle shaped crystals (4.83 g, 56%), m.p. 93.5°-94.5° C. After addition The layers were separated the ether layer was extracted with additional 10% NaOH (10 ml) The combined aqueous layers were washed with ether (30 ml) to give a layer of oil above the water layer This was extracted with Et2O (50 ml×2) The ether extracts were washed with saturated NaCl solution (3×30 ml) dried (MgSO4) The solvent was removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-butylamino-4-oxobutanoic acid (20 mmol) and concentrated sulfuric acid (1 ml) in MeOH (40 ml) is heated at reflux for 8 hours. The reaction is cooled to room temperature and saturated NaHCO3 is carefully added until CO2 gas no longer evolves. Most of the MeOH is removed in vacuo and the residue is partitioned between Et2O (100 ml) and H2O (40 ml). The water layer is re-extracted with Et2O (50 ml). The combined Et2O layers are washed with H2O (20 ml×2) and dried. Filtration and evaporation of solvent gives the title compound. at reflux for 8 hours Most of the MeOH is removed in vacuo the residue is partitioned between Et2O (100 ml) and H2O (40 ml) The water layer is re-extracted with Et2O (50 ml) The combined Et2O layers are washed with H2O (20 ml×2) dried Filtration and evaporation of solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: n-Butylamine (9.05 g, 0.1225 mole) was dissolved in Et2O (30 ml). Succinic anhydride (5 g, finely powdered) was added portionwise. After addition was complete, the heterogeneous mixture was stirred 1 hour at room temperature. The reaction mixture was then poured into 10% NaOH in H2O (10 ml) and Et2O (30 ml). The layers were separated and the ether layer was extracted with additional 10% NaOH (10 ml). The combined aqueous layers were washed with ether (30 ml) and acidified with concentrated HCl to give a layer of oil above the water layer. This was extracted with Et2O (50 ml×2). The ether extracts were washed with saturated NaCl solution (3×30 ml) and dried (MgSO4). The solvent was removed in vacuo to give a white solid (7.5 g) which was recrystallized from benzene to give title acid as needle shaped crystals (4.83 g, 56%), m.p. 93.5°-94.5° C. After addition The layers were separated the ether layer was extracted with additional 10% NaOH (10 ml) The combined aqueous layers were washed with ether (30 ml) to give a layer of oil above the water layer This was extracted with Et2O (50 ml×2) The ether extracts were washed with saturated NaCl solution (3×30 ml) dried (MgSO4) The solvent was removed in vacuo