N,N',N''-[Nitrilotris(2,1-ethanediylthio-2,1-ethanediyl)]tris[5-(diMethylaMino)-1-naphthalenesulfonaMide synthesis

Yield:1350343-28-0 24 mg

Reaction Conditions:

with potassium carbonate in tetrahydrofuran at 25; for 24 h;Inert atmosphere;

Steps:

Synthesis of 4

In a round bottom flask, tris[2-(2-aminoethylthio)ethyl] amine (3) (0.100 g, 0.31 mmol) and K₂CO₃ (0.170 g, 1.22 mmol) were stirred in dry THF for 30 min under an argon atmosphere. Dansyl chloride (0.331 g, 1.23 mmol) was added and the mixture was stirred overnight at room temperature. The resulting insoluble precipitate was removed by filtration. The solvent was removed under vacuum. The crude product was purified by preparative thin layer chromatography, run in the dark (5% MeOH in CH₂Cl₂) to yield 24 mg of a yellow oil, yield 8%). ¹H NMR (300 MHz, CDCl₃) δ 1.66 (s, 3H), 2.43 (t, J = 6.6, 6H), 2.51-2.68 (m, 12H), 2.90 (s, 18H), 3.04-3.10 (m, 6H), 7.19 (d, J = 7.5, 3H), 7.50-7.59 (m, 6H), 8.24-8.32 (m, 6H), 8.55 (d, J = 8.4, 3H), ¹³C NMR (300 MHz, CDCl₃) δ 31.4 (3CH₂), 41.3 (3CH₂), 44.4 (6CH₃), 52.2 (3CH₂), 54.1 (3CH₂), 114.2 (3CH), 114.3 (3C), 117.8 (3CH), 122.2 (3CH), 127.5 (3CH), 128.5 (3CH), 128.5 (3C), 128.9 (3C), 129.5 (3CH), 151.0 (3CH), HRMS calcd for C₄₈H₆₄N₇O₆S₆ (M+H)⁺ 1026.3237, found 1026.2985.

References:

Wanichacheva, Nantanit;Kumsorn, Ploypan;Sangsuwan, Rapeepat;Kamkaew, Anyanee;Lee, Vannajan Sanghiran;Grudpan, Kate [Tetrahedron Letters,2011,vol. 52,# 46,p. 6133 - 6136] Location in patent:experimental part