1H-NMR chemical shifts and coupling constants of dabigatran, dabigatran 1-O-acylglucuronide, and its rearrangement products
Bold entries represent downfield shifted signals at the site of ester linkage.
| Atom no. | Dabigatran | 1-O-Acylglucuronide: H1′-β | 2-O-Acylglucuronide | 3-O-Acylglucuronide | 4-O-Acylglucuronide | |||
|---|---|---|---|---|---|---|---|---|
| H1′-α | H1′-β | H1′-α | H1′-β | H1′-α | H1′-β | |||
| δ (ppm), J (Hz) | ||||||||
| 6 | 7.20 d, 8.4 | 7.17 d, 8.4 | 7.17 d, 8.3 | 7.17 d, 8.3 | 7.6 d, 8.3 | |||
| 7 | 7.59 dd, 1.5 + 8.4 | 7.53 dd, 1.5 + 8.4 | 7.53 dd, 1.5 + 8.4 | 7.54 dd, 1.6 + 8.4 | 7.52 dd, 1.5 + 8.5 | 7.51 dd, 1.5 + 8.5 | 7.52 dd, 1.5 + 8.3 | 7.53 dd, 1.5 + 8.3 |
| 9 | 8.20 d, 1.3 | 8.14 d, 1.4 | 8.15 d, 1.5 | 8.17 d, 1.5 | 8.13 s, broad | 8.15 d, 1.5 | 8.16 d, 1.5 | |
| 10 | 3.58 s | 3.57 s | 3.582 s | 3.578 s | 3.59 s | 3.55 s | 3.56 s | |
| 11 | 4.77 s | 4.77 s | 4.77 s | 4.78 s | 4.76 si | |||
| 14, 18 | 7.16 d, 8.9 | 7.16 d, 8.9 | 7.16 d, 8.8 | 7.16 d, 8.8 | 7.16 d, 9.0 | |||
| 15, 17 | 7.99 d, 8.9 | 7.99 d, 8.9 | 7.99 d, 8.8 | 8.0 d, 8.9 | 7.98 d, 8.8 | |||
| 24 | 4.88 t, 7.7 | 4.70 t, 7.4 | ∼ 4.76–4.80, si | 4.77 t, si | 4.76, si | |||
| 25 | 3.26 t, 7.7 | 3.14 t, 7.4 3.15 t, 7.4 | 3.11–3.20 m | 3.20–3.29 m | 3.17 t, broad | 3.20 m + 3.28 m, broad | ||
| 29 | 7.12 d, 8.0 | 7.07 d, 8.0 | 7.07 d, 8.2 | 7.02 d, 8.05 | 7.08 d, 8.2 | 7.05 d, 8.3 broad | ||
| 30 | 7.37 dt, 1.9 + 7.6 + 7.9 | 7.38 dd, 2.0 + 8.0 | 7.34–7.38, m | 7.34–7.39, m | 7.31–7.35, m | |||
| 31 | 6.95 ddd, 0.9 + 4.9 + 7.3 | 6.95 ddd, 0.8 + 5.3 + 7.5 | 6.94, m | 6.95, m | 6.90–6.94, m | |||
| 32 | 8.49 dd, 1.2 + 4.8 | 8.45 dd, 1.2 + 5.3 | 8.43 dd, 1.7 + 4.8 | 8.43, m | 8.40 + 8.41, 2 × dd, broad | |||
| H-1′ | 6.42 d, 8.1 | 6.15 d, 3.5 | 5.47 d, 8.0 | 5.99 d, 3.5 | 5.46 d, 7.8 | 6.02 d, 3.6 | 5.46 d, 8.0 | |
| H-2′ | 4.29 t, 8.6 | 5.59 dd, 3.5 + 10 | 5.78 dd, ∼8 + 9 | 4.36 dd, 3.4 + 10 | 4.25 dd, 7.5 + 9.5 | 4.34 dd, 3.6 + 9.6 | 4.25 t, 8.3 broad | |
| H-3′ | 4.41 t, 9.0 | 5.01 t, 9.1 + 9.7 | 4.41 t, 9.1 | 6.35 t, 9.5 | 6.00 t, 9.4 | 4.92 t, 9 | 4.47 t, 9.5 | |
| H-4′ | 4.65 t, 9.4 | 4.76 dd, si + 9.5 | 4.66 t, 8.8 | 4.72 t, 9.5 + 9.8 | 4.69 t, 9.75 | 6.05 t, 9.8 | 6.01 t, 9.8 | |
| H-5′ | 4.76 d, 9.6 | 5.42 d, 9.9 | 4.71 d, 9.7 | 5.39 d, 9.7 | 4.72 d, 9.75 | 5.39 d, 9.9 | 4.71 d, 9.9 | |
s, singlet; d, doublet; dd, double-doublet; ddd, double double-doublet; t, triplet; dt, doubletriplet; m, multiplet; si, superimposed (overlapped).