4-Ethylbenzoyl chloride → 4-bromo-3-(4-ethylphenylmethyl)-1-(beta-D-glucopyranosyl)indole
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][O:30]C(=O)C)[C@@H:22]([O:23]C(=O)C)[C@H:17]([O:18]C(=O)C)[C@H:12]1[O:13]C(=O)C.[CH2:34]([C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=O)=[CH:38][CH:37]=1)[CH3:35]>>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:40][C:39]1[CH:43]=[CH:44][C:36]([CH2:34][CH3:35])=[CH:37][CH:38]=1)=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][OH:30])[C@@H:22]([OH:23])[C@H:17]([OH:18])[C@H:12]1[OH:13]Participants
3
Procedure
The above 4-bromo-1-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl)indole and 4-ethylbenzoyl chloride were treated in a manner similar to Example 3 to give the titled compound, 4-bromo-3-(4-ethylphenylmethyl)-1-(β-D-glucopyranosyl)indole as a colorless powder. APCI-Mass m/Z 476/478 (M+H). 1H-NMR (DMSO-d6) δ 1.15 (t, J=7.6 Hz, 3H), 2.56 (q, J=7.5 Hz, 2H), 3.23 (td, J=9.0, 5.5 Hz, 1H), 3.39 (td, J=8.8, 5.1 Hz, 1H), 3.43-3.47 (m, 2H), 3.61-3.69 (m, 2H), 4.26 (s, 2H), 4.53 (t, J=5.3 Hz, 1H), 5.09 (d, J=5.3 Hz, 1H), 5.16 (d, J=5.1 Hz, 1H), 5.20 (d, J=5.8 Hz, 1H), 5.40 (d, J=9.0 Hz, 1H), 7.03 (t, J=7.9 Hz, 1H), 7.09-7.14 (m, 4H), 7.21 (d, J=7.5 Hz, 1H), 7.23 (s, 1H), 7.59 (d, J=8.3 Hz, 1H).
Sources & evidence
- ORD record
- ord-91eb7ad6dac542a28ca0f90e3772f5ac
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935674B2
Reaction notes
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