Design of a Neutral Macrocyclic Ionophore
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organic layer was washed successively with water and brine, dried
with anhydrous Na2SO4, and concentrated under vacuum. The res-
idue was distilled at 120Ϫ130 °C/2Ϫ3 mbar until the evolution of
ethanol and carbon oxide sulfide ceased. The deep brown residue
was then immediately subjected to column chromatography on
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18 (550 mg, 76%) as an orange oil; Rf ϭ 0.75 (ethyl acetate/hexane,
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[18]
3:7). IR (neat): ν˜ ϭ 2102Ϫ2188 (ϪNϭCϭS) cmϪ1. H NMR: δ ϭ
1
2.92 (t, J ϭ 6.8 Hz, 4 H), 3.77 (t, J ϭ 6.8 Hz, 4 H) ppm. 13C NMR:
δ ϭ 32.6 (Ϫ), 45.4 (Ϫ), 133.2 (Cquat) ppm. MS (EI): m/z (%) ϭ 204
(100). HRMS: C6H8N2S3 (203.9848) [Mϩ] ϭ 203.9849 Ϯ 0.3 ppm.
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S)]: A mixture of 17 (355 mg, 1 mmol) and NaOH
(90 mg, 2.2 mmol) in dioxane was stirred with 4 mL of water for
1 h. Compound 18 (204 mg, 1 mmol), dissolved in 4 mL of dioxane,
was then added to this solution. After stirring for 12 h, the mixture
was heated to 70 °C for 4 h, and the solvent was then removed
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ethyl acetate) to yield 8 (X ϭ S) (150 mg, 30%) as a white solid,
729Ϫ730.
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m.p. 175Ϫ176 °C. IR (neat): ν˜ ϭ 3200, 1558 cmϪ1 1H NMR
.
(400 MHz, [D6]DMSO): δ ϭ 2.71 (t, J ϭ 6.8 Hz, 12 H), 3.52Ϫ3.62
(m, 12 H) ppm. 13C NMR (100 MHz, [D6]DMSO): δ ϭ 30.1 (Ϫ),
43.4 (Ϫ), 181.0 (Cquat) ppm. MS(FAB): m/z (%) ϭ 487 (100) [M ϩ
H]ϩ. C15H30N6S6 (486.80): calcd. C 37.03, H 6.22, N 17.28, S 39.46;
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Acknowledgments
there.
This work was supported by the Deutsche Bundesstiftung Umwelt,
which is gratefully acknowledged. T. F. thanks the Grand Duchy
of Luxembourg and the Free State of Bavaria for graduate fellow-
ships. We thank Prof. Michael Göbel for providing us a sample of
compound 19.
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