6-Aminohexanoic Acid → N-(5-Carboxypentyl)maleamic acid

HRID 1661865

Reaktionsgleichung

Reaktionsgleichung von HRID 1661865
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH:12]=[CH:11]1.O>CN(C=O)C>[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:10]([CH:11]=[CH:12][C:13]([OH:15])=[O:14])=[O:16])([OH:9])=[O:8]

Komponenten

5

Edukt 3

HCID 5646-Aminohexanoic AcidHCID 962WaterHCID 7923Maleic Anhydride

Produkt 1

HCID 329056N-(5-Carboxypentyl)maleamic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Aminocaproic acid (10.1 g, 81.6 mmol) was added to maleic anhydride (8.09 g, 82.6 mmol), in 100 mL of anhydrous DMF. The mixture was stirred at room temperature for 24 h and poured into 250 mL of water. White precipitate was filtered, washed with ether and dried (15 g, 86%). 1H NMR (DMSO-d6): δ 1.27-1.33 (2H, m), 1.45-1.54 (4H, m), 2.21 (2H, t, J=7.3), 3.18 (2H, q, J=6.7), 6.24 (1H, d, J=13.0), 6.42 (1H, d, J=12.5), 9.11 (1H, br s), 13.6 (1H, br).

Aufarbeitung

  1. filtrationWhite precipitate was filtered
  2. washwashed with ether
  3. customdried (15 g, 86%)

Quellen und Nachweise

ORD-Eintrag
ord-35ca7d6e04c64c588e0ef9add02642f3
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030459B2

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