4-(2-chloroethoxy)benzoyl Chloride → 4-Chloro-3-(4-(2-chloroethyloxy)phenylmethyl)-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.[Cl:34][CH2:35][CH2:36][O:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=O)=[CH:40][CH:39]=1>>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:42][C:41]1[CH:40]=[CH:39][C:38]([O:37][CH2:36][CH2:35][Cl:34])=[CH:46][CH:45]=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-(2-chloroethyloxy)benzoyl chloride were treated in a manner similar to Example 3 to give the titled compound as a colorless powder. APCI-Mass m/Z 499/501 (M+NH4). 1H-NMR (DMSO-d6) δ 3.24 (td, J=9.2, 4.1 Hz, 1H), 3.39 (td, J=8.7, 5.2 Hz, 1H), 3.43-3.47 (m, 2H), 3.62-3.69 (m, 2H), 3.91-3.93 (m, 2H), 4.19-4.21 (m, 4H), 4.53 (t, J=4.9 Hz, 1H), 5.09 (d, J=4.8 Hz, 1H), 5.15 (d, J=4.7 Hz, 1H), 5.21 (d, J=5.3 Hz, 1H), 5.39 (d, J=9.2 Hz, 1H), 6.87 (d, J=8.5 Hz, 2H), 7.02 (d, J=7.5 Hz, 1H), 7.09 (t, J=7.9 Hz, 1H), 7.15 (d, J=8.7 Hz, 2H), 7.22 (s, 1H), 7.53 (d, J=8.2 Hz, 1H).
Sources & evidence
- ORD record
- ord-01ed075500834e09add59c4421a974d5
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935674B2
Reaction notes
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