p-Anisoyl chloride → 4-Chloro-3-(4-methoxyphenylmethyl)-1-(beta-D-glucopyranosyl)-indole
Reaction equation
[Cl: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.[CH3:34][O:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=O)=[CH:38][CH:37]=1>>[Cl: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]([O:35][CH3:34])=[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
4-Chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 1-(3) and 4-methoxybenzoyl chloride were treated in a manner similar to Example 3 to give the titled compound as a colorless powder. APCI-Mass m/Z 434/436 (M+H). 1H-NMR (DMSO-d6) δ 3.20-3.27 (m, 1H), 3.36-3.48 (m, 3H), 3.60-3.71 (m, 2H), 3.71 (s, 3H), 4.20 (s, 2H), 4.53 (t, J=5.6 Hz, 1H), 5.10 (d, J=5.1 Hz, 1H), 5.16 (d, J=5.0 Hz, 1H), 5.21 (d, J=5.6 Hz, 1H), 5.40 (d, J=9.0 Hz, 1H), 6.84 (d, J=8.7 Hz, 2H), 7.03 (d, J=7.6 Hz, 1H), 7.09 (t, J=7.9 Hz, 1H), 7.15 (d, J=8.7 Hz, 2H), 7.20 (s, 1H), 7.54 (d, J=8.2 Hz, 1H).
Sources & evidence
- ORD record
- ord-99700be93b194fffaa4c68abb67c7bed
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935674B2
Reaction notes
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