4-Hydrazinobenzenesulfonic acid → 6-(2,3-dimethyl-5-sulfo-3H-indol-3-yl)hexanoic acid

HRID 1435160

Reaktionsgleichung

Reaktionsgleichung von HRID 1435160
[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)N.[C:13]([CH:16]([CH3:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])(=O)[CH3:14]>C(O)(=O)C.O.CO>[CH3:14][C:13]1[C:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])([CH3:25])[C:8]2[C:3](=[CH:4][CH:5]=[C:6]([S:9]([OH:12])(=[O:11])=[O:10])[CH:7]=2)[N:1]=1

Komponenten

5

Edukt 2

HCID 668254-Hydrazinobenzenesulfonic acidHCID 222668237-Methyl-8-oxononanoic acid

Produkt 1

HCID 598554226-(2,3-dimethyl-5-sulfo-3H-indol-3-yl)hexanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

To a stirred solution of 4-hydrazinobenzenesulfonic acid (Aldrich, 11.25 g, 0.06 mol) in acetic acid (50 ml) was added 7-acetyloctanoic acid (16.7 g, 0.09 mol). The reaction mixture was heated under reflux for 12 hrs. Acetic acid was removed under reduced pressure. The resulting solid was dissolved in methanol and reprecipitated with a saturated solution of potassium hydroxide in isopropanol. The solid was filtered, washed with isopropanol and dried, (8 g, 40%). The analytical sample was obtained by C18 reversed phase column chromatography using water/methanol mixture as solvent., m.p. 250° C. dec; IR νcm−1=2930, 2597, and 1719. 1H NMR, D2O, δ, 7.8-7.9 (m, 2H, 4-H and 6-H of aromatic protons); 7.6 (d, J=7 Hz, 1H, 7-H of aromatic); 2.2 (t, J=7 Hz, 2H, —CH2—COOH); 1.9-2.1 (m, 2H, alkyl); 1.2-1.6 (a singlet merged in a multiplet, 7H, —CH3 & (—CH2)2); 0.6-0.9 (m, 2H, alkyl).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 12 hrs
  3. customAcetic acid was removed under reduced pressure
  4. dissolutionThe resulting solid was dissolved in methanol
  5. customreprecipitated with a saturated solution of potassium hydroxide in isopropanol
  6. filtrationThe solid was filtered
  7. washwashed with isopropanol
  8. customdried
  9. customThe analytical sample was obtained by C18 reversed phase column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7daacfb2ad2947f581353dc1207e0f0a
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615646B2

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