4-Chlorobenzoyl chloride → 4-Bromo-3-(4-chlorophenylmethyl)-1-(beta-D-glucopyranosyl)indole

HRID 544906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544906
[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.[Cl:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=O)=[CH:37][CH:36]=1>>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:39][C:38]1[CH:42]=[CH:43][C:35]([Cl:34])=[CH:36][CH:37]=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]

Komponenten

3

Edukt 2

HCID 85014-Chlorobenzoyl chlorideHCID 671978654-bromo-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Produkt 1

HCID 671983594-Bromo-3-(4-chlorophenylmethyl)-1-(beta-D-glucopyranosyl)indole

Versuchsvorschrift

The titled compound was prepared from 4-bromo-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 22-(1) and 4-chlorobenzoyl chloride in a manner similar to Example 27 as a colorless powder. APCI-Mass m/Z 482/484 (M+H). 1H-NMR (DMSO-d6) δ 3.21-3.28 (m, 1H), 3.33-3.39 (m, 3H), 3.62-3.71 (m, 2H), 4.28 (s, 2H), 4.54 (t, J=5.5 Hz, 1H), 5.11 (d, J=5.3 Hz, 1H), 5.17 (d, J=5.1 Hz, 1H), 5.23 (d, J=5.8 Hz, 1H), 5.41 (d, J=9.0 Hz, 1H), 7.04 (t, J=7.9 Hz, 1H), 7.19-7.24 (m, 3H), 7.30-7.35 (m, 2H), 7.33 (brs, 1H), 7.60 (d, J=8.3 Hz, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-809d51c4d5184c33a410c523f669eca8
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935674B2

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