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

HRID 1808659

반응식

HRID 1808659 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 5736836-Maleimidohexanoic acid

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3223683fad684daf8647487fbe368583
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08361442B2

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