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

HRID 1808659

反応式

HRID 1808659 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 5736836-Maleimidohexanoic acid

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3223683fad684daf8647487fbe368583
出典データセット
uspto-grants-2013_01
特許番号
US08361442B2

関連ノート

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