Spermine → Tetratosylspermine

HRID 1490147Notes

Reaction equation

HRID 1490147 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH2:14].[OH-:15].[Na+].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(Cl)Cl>[S:23]([C:13]([S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])([CH2:12][CH2:11][NH:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3][CH2:2][NH2:1])[N:14]([S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:24])=[O:15])([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 1103SpermineHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 23440082TetratosylspermineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N1,N2, N3, N4 -Tetra-p-tosylspermine, To spermine tetrahydrocbloride (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 0.5 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-25780140489448b08376ec9c2e27ed98
Source dataset
uspto-grants-1997_10
Patent number
US05681837

Reaction notes

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