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pressure, and extracted with methanol several times. The com-
bined organic layers were concentrated to afford azimic acid 4
(34 mg, yield: 76%) as a pale yellow solid {mp 212–214 °C (MeOH);
lit. mp 214–215 °C;8f mp 212–215 °C;6
½
a 2D0
ꢀ
¼ þ7:7 (c 0.5, MeOH);
lit. ½a 2D0
ꢀ
¼ þ8:0 (c 1.0, MeOH);8f
½
a 2D3
ꢀ
¼ þ7:45 (c 0.49, MeOH)6}. IR
(film) m .
max: 3339, 1709, 2853, 1409, 1260, 1200, 1090, 1020 cmꢁ1
1H NMR (400 MHz, CD3OD): d 1.36 (d, J = 6.5 Hz, 3H, CH3), 1.42–
1.89 (m, 11H), 1.95–2.05 (m, 1H), 2.35 (t, J = 7.3 Hz, 2H, COCH2),
3.08–3.16 (m, 1H, H-6), 3.26 (dq, J = 6.5, 1.4 Hz, 1H, H-2), 3.88 (t,
J = 1.4 Hz, 1H, H-3). 13C NMR (100 MHz, CD3OD): d 15.9, 23.5,
25.7, 25.9, 29.8, 31.0, 34.5, 34.8, 57.5 (NCH), 58.5 (NCH), 65.8 (C-
3), 177.6 (C@O). MS (ESI): 230 (MH+, 100). HRESIMS calcd for
[C12H23NO3 + H]+: 230.1751; found: 230.1750.
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Acknowledgments
The authors are grateful to the NSF of China (grant numbers:
20772099; 20832005, NFFTBS (No. J0630429) and the program
for Innovative Research Team in Science & Technology (University)
in Fujian Province for financial support.
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