4-Toluenesulfonyl chloride → Tetratosylspermine

HRID 1743071Notes

Reaction equation

HRID 1743071 reaction equation
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]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 9384Spermine hydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 23440082TetratosylspermineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 0.5 N 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.

Workup

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

Sources & evidence

ORD record
ord-b4e360d43a5542debcc9b3ae07702d65
Source dataset
uspto-grants-1994_08
Patent number
US05342945

Reaction notes

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