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

HRID 1435160

반응식

HRID 1435160 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 22242641Methanol--water (1/1)용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7daacfb2ad2947f581353dc1207e0f0a
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615646B2

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