4-Toluenesulfonyl chloride → Tetratosylspermine

HRID 400296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400296
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-toluenesulfonyl 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-469d670d79ae4998b8445d4495fc9d3e
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05827894

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