4-Toluenesulfonyl chloride → Tetratosylspermine

Participants

Reaction Steps

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 0.5 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. NMR (CDCl3) δ7.2-7.9 (m, 16H), 5.34 (t, 2H, J=7), 2.9-3.3 (m, 12H), 2.43 (s, 12H), 1.5-2.0 (m, 8H).

Provenance & Evidence