4-Methylbenzoyl Chloride → 4-Chloro-3-(4-methylphenylmethyl)-1-(beta-D-glucopyranosyl)indole

HRID 544871Notes

Reaction equation

HRID 544871 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][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=O)=[CH:37][CH:36]=1>>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:34][C:35]1[CH:43]=[CH:42][C:38]([CH3:39])=[CH:37][CH:36]=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

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 670203794-Chloro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Product 1

HCID 671987334-Chloro-3-(4-methylphenylmethyl)-1-(beta-D-glucopyranosyl)indole

Procedure

4-Chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 1-(3) and 4-methylbenzoyl chloride were treated in a manner similar to Example 2-(4), (5), (6) and (7) to give the titled compound as a colorless powder. APCI-Mass m/Z 418/420 (M+H). 1H-NMR (DMSO-d6) δ 2.25 (s, 3H), 3.21-3.25 (m, 1H), 3.32-3.39 (m, 1H), 3.43-3.47 (m, 2H), 3.61-3.69 (m, 2H), 4.22 (s, 2H), 4.53 (t, J=5.5 Hz, 1H), 5.01 (d, J=5.3 Hz, 1H), 5.15 (d, J=5.0 Hz, 1H), 5.20 (d, J=5.8 Hz, 1H), 5.39 (d, J=9.2 Hz, 1H), 7.06-7.12 (m, 5H), 7.21 (s, 1H), 7.53 (d, J=8.2 Hz, 1H).

Sources & evidence

ORD record
ord-ec3836771fb84ee69a9e87569e8cdf8b
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

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