4-Toluenesulfonyl chloride → Tetratosylspermine

HRID 1535035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1535035
Cl.Cl.Cl.Cl.[NH2:5][CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][NH2:18].[OH-:19].[Na+].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[S:27]([C:17]([S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28])([CH2:16][CH2:15][NH:14][CH2:13][CH2:12][CH2:11][CH2:10][NH:9][CH2:8][CH2:7][CH2:6][NH2:5])[N:18]([S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28])[S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:28])=[O:19])([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28]

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 9384Spermine hydrochlorideHCID 14798Sodium Hydroxide

Produkt 1

HCID 23440082TetratosylspermineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To spermine tetrahydrochloride (4.53 g, 13.0 mmol) and 10% aqueous NaOH (200 mL, 132 mmol) at 0° is added dropwise p-toluene-sulfonyl chloride (9.98 g, 52.3 mmol) in CH2Cl2 with rapid stirring. After 1 hr the mixture is allowed to warm to room temperature and to stir for 2 days. The organic phase is separated and washed with 0.5N HCl, H2O, and brine, dried over Na2SO4 and purified on silica gel (450 g, 3% MeOH/CHCl3) to give 9.69 g, 91% yield of tetratosylspermine.

Aufarbeitung

  1. customThe organic phase is separated
  2. washwashed with 0.5N HCl, H2O, and brine
  3. dry with materialdried over Na2SO4
  4. custompurified on silica gel (450 g, 3% MeOH/CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-08ae0cec8ada43f395b9ab745289cacd
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05091576

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