Table 3.
1H and 13C NMR assignments for Eze-4, ezetimibe and desfluoro ezetimibe.
| Positiona |
1H-δ ppm |
13C-δ ppm (DEPT) |
||||
|---|---|---|---|---|---|---|
| Eze-4c | Ezetimibeb | Desfluoro ezetimibeb | Eze-4c | Ezetimibeb | Desfluoro ezetimibeb | |
| 1 | – | – | – | 172.5 (C) | 168.1 (C) | 168.3 (C) |
| 2 | 2.81 (dt, J=7.5, 3.0 Hz, 2H) | 3.04–3.08 (m, 1H) | 3.03 (br, 1H) | 35.4 (CH2) | 60.1 (CH) | 59.9 (CH) |
| 3 | 1.22–1.33 (m, 2H) | 1.60–1.83 (m, 2H) | 1.60–1.83 (m, 2H) | 18.3 (CH2) | 25.2 (CH2) | 25.3 (CH2) |
| 4 | 1.83–1.90 (m, 2H) | 1.60–1.83 (m, 2H) | 1.60–1.83 (m, 2H) | 36.5 (CH2) | 37.1 (CH2) | 37.1 (CH2) |
| 5 | – | 4.47 (m, 1H) | 4.45 (br, 1H) | 103.2 (C) | 71.8 (CH) | 71.7 (CH) |
| 6 | – | – | – | 136.6 (d, 4J=3.2 Hz, C) | 142.9 (d, 4J=2.9 Hz, C) | 142.9 (d, 4J=2.9 Hz, C) |
| 7 | 7.25 (dd, J=8.1, 1.8 Hz, 2H) | 7.07–7.31 (m, 2H) | 7.06–7.29 (m, 2H) | 129.0 (d, 3J=7.7 Hz, 2CH) | 128.2 (d, 3J=6.2 Hz, 2CH) | 128.2 (d, 3J=7.7 Hz, 2CH) |
| 8 | 7.00 (dt, J=8.7, 1.8 Hz, 2H) | 6.74 (d, J=8.4 Hz, 2H) | 6.72 (d, J=8.1 Hz, 2H) | 115.1 (d, 2J=21 Hz, 2CH) | 115.4 (d, 2J=21 Hz, 2CH) | 115.4 (d, 2J=21 Hz, 2CH) |
| 9 | – | – | – | 162.5 (d, 1J=245 Hz, C) | 161.7 (d, 1J=241 Hz, C) | 161.7 (d, 1J=240 Hz, C) |
| 10 | 3.11 (s, 3H) | 5.28 (d, J=4.5 Hz, 1H) | 5.26 (br, 1H) | 48.8 (CH3) | – | – |
| 11 | 3.09 (s, 3H) | 4.79 (d, J=2.1 Hz, 1H) | 4.77 (br, 1H) | 48.8 (CH3) | 60.3 (CH) | 60.0 (CH) |
| 12 | – | – | – | 154.0 (C) | 128.6 (C) | 128.8 (C) |
| 13 | 4.25 (dd, J=9.0, 3.6 Hz, 1H); 4.65 (t, J=9.0 Hz, 1H) | 7.07–7.31 (m, 4H) | 7.06–7.29 (m, 4H) | 70.2 (CH2) | 128.25 (2CH) | 128.19 (2CH) |
| 14 | 5.36 (dd, J=8.4, 3.6 Hz, 1H) | 57.7 (CH) | 116.4 (2CH) | 116.4 (2CH) | ||
| 15 | – | – | – | 139.3 (C) | 158.1 (C) | 158.0 (C) |
| 16 | 7.32–7.42 (m, 5H) | 9.53 (s, 1H) | 9.50 (s, 1H) | 126.1 (2CH) | – | – |
| 17 | – | – | 129.4 (2CH) | 134.7 (d, 4J=2.0 Hz, C) | 138.2 (C) | |
| 18 | 7.07–7.31 (m, 4H) | 7.06–7.29 (m, 4H) | 129.0 (CH) | 119.0 (d, 3J=7.7 Hz, 2CH) | 117.3 (2CH) | |
| 19 | – | – | 116.6 (d, 2J=22 Hz, 2CH) | 129.7 (2CH) | ||
| 20 | – | – | 6.98 (t, J=7.2 Hz, 1H) | – | 158.7 (d, 1J=239 Hz, C) | 124.1 (CH) |
Assignments: s: singlet; d: doublet; t: triplet; m: multiplet; br: broad singlet. Mean values used for coupled signals.
a
Numbering of all compounds shown in Fig. 2 and copies of NMR spectra are presented in Appendix A.
b
Solvent is DMSO-d6.
c
Solvent is CDCl3.