6-Aminohexanoic Acid → 6-Maleimidohexanoic acid

HRID 1017121

Reaction equation

HRID 1017121 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([CH2:14][CH2:15][NH2:16])[CH2:9][CH2:10][C:11]([OH:13])=[O:12]>C(O)(=O)C>[C:1]1(=[O:6])[N:16]([CH2:15][CH2:14][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[C:4](=[O:5])[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 7923Maleic Anhydride

Product 1

HCID 5736836-Maleimidohexanoic acidYield 75.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

A solution of maleic anhydride (0.05 mole) in acetic acid (20 mL) was mixed with a solution of ε-Amino-n-caproic acid (0.05 mole) in acetic acid (50 mL) and stirred at room temperature for 2 hours. An additional amount of acetic acid (150 mL) was added and the reaction mixture refluxed for 16 hours. The reaction mixture was evaporated under vacuo to an oil and chloroform was then added (50 mL). The solution was left to stand for 16 hours at room temperature whereupon impurities were precipitated out of the solution. The precipitate was filtered and the filtrate was collected, evaporated under vacuo and chromatographed on silica gel using chloroform:acetic acid (95:5) to give 6-Maleimidocaproic acid 23 (8 g).

Workup

  1. temperaturethe reaction mixture refluxed for 16 hours
  2. customThe reaction mixture was evaporated under vacuo to an oil and chloroform
  3. additionwas then added (50 mL)
  4. waitThe solution was left
  5. waitto stand for 16 hours at room temperature whereupon impurities
  6. customwere precipitated out of the solution
  7. filtrationThe precipitate was filtered
  8. customthe filtrate was collected
  9. customevaporated under vacuo
  10. customchromatographed on silica gel

Sources & evidence

ORD record
ord-fdc493cdd95e455b8f79d9c6bd9ce8cf
Source dataset
uspto-grants-2002_11
Patent number
US06479265B1

Linked notes

Loading…