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

HRID 1808659

Reaktionsgleichung

Reaktionsgleichung von HRID 1808659
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 5736836-Maleimidohexanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3223683fad684daf8647487fbe368583
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08361442B2

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