4-Pivaloyloxybenzoyl chloride → 4-chloro-3-(4-pivaloyloxyphenylmethyl)-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

HRID 544908Notes

Reaction equation

HRID 544908 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:31](=[O:33])[CH3:32])[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]1[O:13][C:14](=[O:16])[CH3:15].[C:34]([O:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](Cl)=O)=[CH:43][CH:42]=1)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:45][C:44]1[CH:43]=[CH:42][C:41]([O:40][C:34](=[O:39])[C:35]([CH3:37])([CH3:36])[CH3:38])=[CH:49][CH:48]=1)=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]1[O:13][C:14](=[O:16])[CH3:15]

Participants

3

Reactant 2

HCID 136043274-Pivaloyloxybenzoyl chlorideHCID 670203794-Chloro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

Product 1

HCID 671988344-chloro-3-(4-pivaloyloxyphenylmethyl)-1-(2,3,4,6-tetra-O-acetyl-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-pivaloyloxybenzoyl chloride were treated in a manner similar to Example 2-(4), (5) and 27-(3) to give 4-chloro-3-(4-pivaloyloxyphenylmethyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole as a colorless powder. APCI-Mass m/Z 689/691 (M+NH4).

Sources & evidence

ORD record
ord-4e36443164644c4cbed3d944095fd0bf
Source dataset
uspto-grants-2011_05
Patent number
US07935674B2

Reaction notes

Loading…