Hydrochloric Acid → HCID 68745664, compound

HRID 2354293Notes

Reaction equation

HRID 2354293 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@H:10]1[C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][C:47]=2[CH3:49])[NH:42][CH:41]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:52]([C:54]1[CH:61]=[CH:60][C:57]([CH2:58]Br)=[CH:56][CH:55]=1)[CH3:53].Cl>CN(C)C=O>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:11][C@H:10]1[C:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][C:47]=2[CH3:49])[N:42]([CH2:58][C:57]2[CH:60]=[CH:61][C:54]([CH2:52][CH3:53])=[CH:55][CH:56]=2)[CH:41]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 122315601-(Bromomethyl)-4-ethylbenzeneHCID 57616156HCID 57616156, compound

Product 1

HCID 68745664HCID 68745664, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4-methyl-1H-indole (150 mg) in N,N-dimethylformamide (2 mL) was added 55% sodium hydride (12 mg) under ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. To this mixture was added 4-ethylbenzyl bromide (55 mg) at the same temperature, and the mixture was stirred at the same temperature for 15 minutes, and stirred at room temperature for 1 hour. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with diethylether. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was washed with a mixed solvent of n-hexane and diethyl ether (10/1), and dried under reduced pressure to give 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-(4-ethyl-benzyl)-4-methyl-1H-indole (139 mg). This material (125 mg) was dissolved in a mixed solvent of methanol (2 mL) and tetra hydrofuran (2 mL). To the solution was added 10% palladium-carbon powder (50 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 4 hours. The insoluble material was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=8/1) to give the title compound (58 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 15 minutes
  3. stirringstirred at room temperature for 1 hour
  4. extractionthe resulting mixture was extracted with diethylether
  5. washThe extract was washed with water and brine successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. washThe residue was washed with a mixed solvent of n-hexane and diethyl ether (10/1)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-e213a3a512994468818a56b538b038bf
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

Loading…