A. Zall et al. / Bioorg. Med. Chem. 19 (2011) 4903–4909
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4909
7.24–7.19 (m, 1H), 6.90 (d, J = 2.2 Hz, 1H), 6.85 (dd, J = 8.5, 2.2 Hz,
1H), 4.43 (t, J = 6.3 Hz, 2H), 4.23 (t, J = 7.3 Hz, 2H), 3.74–3.69 (m,
2H), 1.90–1.82 (m, 2H), 1.44–1.23 (m, 10H), 0.89 (t, J = 7.0 Hz,
3H) ppm, 13C NMR (75 MHz, CDCl3): d = 157.3, 141.6, 140.7,
124.6, 122.9, 121.1, 119.6, 118.9, 117.5, 109.5, 107.3, 94.8, 68.6,
43.1, 31.8, 29.4, 29.3, 29.2, 28.8, 27.3, 22.6, and 14.0 ppm.
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3.5. 2-(9-Octyl-9H-carbazol-2-yloxy)-ethanesulfonic acid 18
To a solution of 13 (BSc4004) (0.020 g, 0.05 mmol) in a mixture
of H2O (0.050 mL) and dioxane (0.050 mL) was added Na2SO3
(0.032 g, 0.25 mmol) and the resulting mixture was heated at
160 °C under microwave irradiation until the reaction was com-
pleted (TLC control). The reaction mixture was concentrated in va-
cuo, the resulting solid dissolved in EtOHabs and concentrated in
vacuo to give 0.007 g (35%) of 18 (BSc4079) as a colorless solid.
HPLC: 7.0 min (93%), 1H NMR (500 MHz, MeOD): d = 7.97–7.94
(m, 1H), 7.93 (d, J = 8.5 Hz, 1H), 7.41 (d, J = 8.2 Hz, 1H), 7.37–7.30
(m, 1H), 7.18–7.10 (m, 1H), 6.84 (dd, J = 8.5, 2.2 Hz, 1H), 7.04 (d,
J = 2.1 Hz, 1H), 4.32 (t, J = 7.1 Hz, 2H), 4.53–4.47 (m, 2H), 3.38–
3.33 (m, 2H), 1.89–1.81 (m, 2H), 0.86 (m, 10H), 1.32–1.24 (t,
J = 7.0 Hz, 3H) ppm, 13C NMR (125 MHz, MeOD): d = 143.1, 142.0,
125.3, 124.3, 121.8, 120.2, 119.8, 118.2, 109.7, 109.1, 100.5, 95.2,
65.3, 51.9, 43.7, 32.9, 30.7, 30.3, 29.9, 28.2, 23.6, and 14.4 ppm,
MS (m/z, 70 eV, ESI) = 402 [Mꢁ].
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Supplementary data
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Supplementary data associated with this article can be found, in
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