N-(5-Carboxypentyl)maleamic acid → 6-Maleimidohexanoic acid

HRID 1661866

Reaction equation

HRID 1661866 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([CH:12]=[CH:13][C:14]([OH:16])=O)=[O:11])([OH:3])=[O:2].CC([O-])=O.[Na+]>O(C(C)=O)C(C)=O>[O:16]=[C:14]1[CH:13]=[CH:12][C:10](=[O:11])[N:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:1]([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 329056N-(5-Carboxypentyl)maleamic acidHCID 517045Sodium Acetate

Product 1

HCID 5736836-Maleimidohexanoic acid

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The acid 14 (4.5 g, 21 mmol) was refluxed in 60 mL of (Ac)2O with NaOAc (1.72 g, 21 mmol) for 3 h. After cooling, the reaction mixture was concentrated. The residue was dissolved in EtOAc, washed with brine, dried over MgSO4, filtered and evaporated to give a deep red oil that was purified by silica gel column chromatography (CHCl3:MeOH/99:1). The maleimide product 15 was isolated as a white solid (1.4 g, 32%). 1H NMR (DMSO-d6): δ 1.18-1.24 (2H, m), 1.45-1.52 (4H, m), 2.18 (2H, t, J=7.5), 3.38 (2H, t, J=7.0), 7.01 (2H, s).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a deep red oil that
  9. customwas purified by silica gel column chromatography (CHCl3:MeOH/99:1)

Sources & evidence

ORD record
ord-2c1698d60ba24d6c979635b6666a6793
Source dataset
uspto-grants-2011_10
Patent number
US08030459B2

Linked notes

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