Citric Acid → Phthalylglycine aldehyde

HRID 1166139Notes

Reaction equation

HRID 1166139 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].C(N(CC)CC)C.S(=O)(=O)=O.N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O.C(Cl)Cl>[O:14]=[C:5]1[C:6]2[C:7](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:9])[N:4]1[CH2:3][CH:2]=[O:1]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 77499N-(2-Hydroxyethyl)phthalimideHCID 168533Sulfur trioxide-pyridine

Product 1

HCID 76201Phthalylglycine aldehydeYield 32%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-hydroxyethyl)phthalimide (1.92 g, 10 mmol) and triethylamine (7 mL, 50 mmol) in DMSO (25 mL) was added solid pyridine sulfur trioxide (4.8 g, 30 mmol) by portions. The resulting mixture was stirred at room temperature for 1 h. The reaction mixture is poured into a mixture of CH2Cl2 and 0.5N aq. citric acid. The layers were separated and the organic layer was washed with water and brine. The organic phase was dried (Na2SO4), and the solvent was removed in vacuo. The resultant residue was purified by flash chromatography (SiO2, 1:1 ethyl acetate/hexane) to provide the title compound (0.6 g, 32%). MS 190 (M+H)+.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with water and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customthe solvent was removed in vacuo
  5. customThe resultant residue was purified by flash chromatography (SiO2, 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fc4203b5435440dba410a7b0a369f72f
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

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