Water → HCID 66765671, compound

HRID 556781Notes

Reaction equation

HRID 556781 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C@@H:10]3[O:39][C@H:38]([CH2:40][O:41][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C@@H:29]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C@H:20]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C@H:11]3[O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:51][C:52]1[CH:59]=[CH:58][C:55]([CH2:56]Cl)=[CH:54][CH:53]=1.O>CN(C)C=O>[CH3:51][C:52]1[CH:59]=[CH:58][C:55]([CH2:56][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C@@H:10]4[O:39][C@H:38]([CH2:40][O:41][CH2:42][C:43]5[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=5)[C@@H:29]([O:30][CH2:31][C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=5)[C@H:20]([O:21][CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[C@H:11]4[O:12][CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:8]=3)[CH:3]=[CH:2]2)=[CH:54][CH:53]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77224-Methylbenzyl chlorideHCID 24758Sodium hydrideHCID 66765790HCID 66765790, compound

Product 1

HCID 66765671HCID 66765671, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(1H-indol-6-yl)-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose (0.13 g) in N,N-dimethylformamide (2 mL) was added sodium hydride (60%, 0.01 g) at 0° C., and the mixture was stirred for 10 minutes. To the mixture was added 4-methylbenzylchloride (0.032 g), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, and the mixture was extracted with diethyl ether. The organic layer washed with water and brine and dried over anhydrous magnesium 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) to give the title compound (0.12 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-20e3ad8820df4863afd665d1e0829467
Source dataset
uspto-grants-2011_11
Patent number
US08058245B2

Reaction notes

Loading…