N. Chen, W. Jia, J. Xu
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(S)-2-(Benzylamino)-3-phenylpropane-1-sulfonic Acid (4h): Colorless
crystals; yield 1.30 g, 85%; m.p. 314–316 °C (decomp.). H NMR
1
(400 MHz, [D6]DMSO): δ = 9.21 (br. s, 1 H, OH), 9.10 (br. s, 1 H,
NH), 7.52–7.26 (m, 10 H, ArH), 4.47–4.38 (m, 1 H, CH2N), 4.37–
4.28 (m, 1 H, CH2N), 3.66 (m, 1 H, CHN), 3.33 (dd, J = 3.8,
13.2 Hz, 1 H, CH2S), 2.89 (dd, J = 11.0, 13.2 Hz, 1 H, CH2S), 2.82
(dd, J = 9.8, 14.5 Hz, 1 H, CH2Ar), 2.62 (dd, J = 2.4, 14.5 Hz, 1
H, CH2Ar) ppm. 13C NMR (100.6 MHz, [D6]DMSO): δ = 136.6,
132.6, 130.0, 129.9, 129.5, 129.4, 129.2, 127.5, 57.1, 49.4, 48.1,
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35.7 ppm. IR (KBr): ν = 3432 (br., OH, NH), 1256 (S=O), 1170
˜
(S=O) cm–1. HRMS (ESI): calcd. for C16H20NO3S [M + H]+
306.1158; found 306.1151.
1-Aminohexane-2-sulfonic Acid (4m): Colorless crystals; yield
798 mg, 88%; m.p. 335 °C (decomp.). 1H NMR (300 MHz, D2O,
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13.8 Hz, 1 H, CH2N), 3.15 (dd, J = 9.0, 13.8 Hz, 1 H, CH2N), 2.95
(m, 1 H, CHS), 1.79 (m, 1 H, CH2), 1.33 (m, 5 H, 2 CH2 + 1 H of
CH2), 0.78 (t, J = 7.2 Hz, 3 H, CH3) ppm. 13C NMR (75.5 MHz,
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˜
4543–4546.
1221 (S=O), 1150 (S=O) cm–1. MS (ESI): m/z = 181.7 [M + H]+,
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Supporting Information (see also the footnote on the first page of
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Acknowledgments
This work was supported by the National Natural Science Founda-
tion of China (20973013) and the Beijing Natural Science Founda-
tion (2092022).
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Received: July 9, 2009
Published Online: October 1, 2009
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