Water → HCID 57616185, compound

HRID 2354295Notes

Reaction equation

HRID 2354295 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]([Cl: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+].[Si]([O:69][CH2:70][CH2:71][C:72]1[CH:79]=[CH:78][C:75]([CH2:76]Br)=[CH:74][CH:73]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.O>CN(C)C=O.O1CCCC1>[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]([Cl:49])[CH:45]=[CH:46][CH:47]=2)[N:42]([CH2:76][C:75]2[CH:78]=[CH:79][C:72]([CH2:71][CH2:70][OH:69])=[CH:73][CH:74]=2)[CH:41]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 57616203HCID 57616203, compoundHCID 57616335HCID 57616335, compound

Product 1

HCID 57616185HCID 57616185, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-chloro-1H-indole (0.48 g) in N,N-dimethylformamide (5 mL) was added 55% sodium hydride (37 mg) under ice-cooling, and the mixture was stirred at the same temperature for 15 minutes. To this mixture was added a solution of 4-[2-(tert-butyldiphenylsilyloxy)ethyl]benzyl bromide (0.42 g) in tetra hydrofuran (2 mL) 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 water, 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. The residue was dissolved in tetra hydrofuran (5 mL). To the solution was added tetra(n-butyl)ammonium fluoride (1.0 mol/L tetra hydrofuran solution, 1.07 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, 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. The residue was washed with a mixed solvent of n-hexane and ethyl acetate (5/1), and dried under reduced pressure to give the title compound (0.50 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 ethyl acetate
  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. dissolutionThe residue was dissolved in tetra hydrofuran (5 mL)
  9. additionTo the solution was added tetra(n-butyl)ammonium fluoride (1.0 mol/L tetra hydrofuran solution, 1.07 mL)
  10. stirringthe mixture was stirred at room temperature for 30 minutes
  11. additionThe reaction mixture was poured into water
  12. extractionthe resulting mixture was extracted with ethyl acetate
  13. washThe extract was washed with water and brine successively
  14. dry with materialdried over anhydrous sodium sulfate
  15. customThe solvent was removed under reduced pressure
  16. washThe residue was washed with a mixed solvent of n-hexane and ethyl acetate (5/1)
  17. customdried under reduced pressure

Sources & evidence

ORD record
ord-4ff221f8b8464250a64caba72e5e9b17
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

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