Sodium Hydroxide → HCID 66886312, compound

HRID 2353019Notes

Reaction equation

HRID 2353019 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[CH:8]=[CH:7]2.[CH3:19][C:20]([O:22][CH2:23][C@H:24]1[O:29][C@H:28](Br)[C@H:27]([O:31][C:32]([CH3:34])=[O:33])[C@@H:26]([O:35][C:36]([CH3:38])=[O:37])[C@@H:25]1[O:39][C:40]([CH3:42])=[O:41])=[O:21].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(Cl)Cl>[C:32]([O:31][C@@H:27]1[C@@H:26]([O:35][C:36](=[O:37])[CH3:38])[C@H:25]([O:39][C:40](=[O:41])[CH3:42])[C@@H:24]([CH2:23][O:22][C:20](=[O:21])[CH3:19])[O:29][C@H:28]1[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[CH:8]=[CH:7]2)(=[O:33])[CH3:34]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 57584215HCID 57584215, compound

Product 1

HCID 66886312HCID 66886312, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 7-hydroxy-1-(4-methylbenzyl)-1H-indole (1.36 g), acetobromo-α-D-glucose (2.59 g) and benzyltri-(n-butyl)ammonium chloride (1.79 g) in methylene chloride (20 mL) was added 5 mol/L aqueous sodium hydroxide solution (3.4 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate 1/1), and purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1-2/1) to give 7-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1-(4-methylbenzyl)-1H-indole (1.25 g). The obtained 7-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1-(4-methylbenzyl)-1H-indole (0.3 g) was dissolved in methanol (2 mL). To the solution was added sodium methoxide (28% methanol solution, 0.05 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by column chromatography on silica gel (eluent: methylene chloride/methanol=5/1) to give the title compound (0.19 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate 1/1)
  2. custompurified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1-2/1)

Sources & evidence

ORD record
ord-7fdc630b54ff434cafea8e6f47a5190a
Source dataset
uspto-grants-2010_07
Patent number
US07749972B2

Reaction notes

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