Hydrochloric Acid → HCID 68743397, compound

HRID 2354296Notes

Reaction equation

HRID 2354296 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](=[C:44]([CH3:49])[CH:45]=[CH:46][CH:47]=2)[NH:42][CH:41]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:53][C:54]1[CH:63]=[CH:62][C:57]([C:58]([O:60][CH3:61])=[O:59])=[CH:56][CH:55]=1.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](=[C:44]([CH3:49])[CH:45]=[CH:46][CH:47]=2)[N:42]([CH2:53][C:54]2[CH:55]=[CH:56][C:57]([C:58]([O:60][CH3:61])=[O:59])=[CH:62][CH:63]=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 256687Methyl 4-(bromomethyl)benzoateHCID 57616256HCID 57616256, compound

Product 1

HCID 68743397HCID 68743397, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-methyl-1H-indole (0.28 g) in N,N-dimethyl-formamide (4 mL) was added 55% sodium hydride (22 mg) under ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. To this mixture was added methyl 4-(bromo-methyl)benzoate (0.12 g) 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 diethyl ether. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1-3/1) to give 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-[4-(methoxycarbonyl)benzyl]-7-methyl-1H-indole (0.32 g). This material was dissolved in a mixed solvent of ethanol (5 mL) and tetra hydrofuran (2.5 mL). To the solution was added potassium hydroxide (0.45 g), and the mixture was stirred at 50° C. overnight. The reaction mixture was poured into 1 mol/L hydrochloric acid (10 mL), and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the title compound (0.31 g)

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 diethyl ether
  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. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1-3/1)

Sources & evidence

ORD record
ord-bf8fda57c6444dcea40fe625b795ceb3
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

Loading…