Water → HCID 68522204, compound

HRID 884117Notes

Reaction equation

HRID 884117 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][CH:20]=2)=[N:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:35][CH2:36][O:37][CH3:38].O>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]([CH2:35][CH2:36][O:37][CH3:38])[C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:24]=2)=[N:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 68524343HCID 68524343, compound

Product 1

HCID 68522204HCID 68522204, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, to a solution of ethyl 3-[4-(5-benzyloxycarbonylaminopyridin-2-yloxy)phenyl]propionate (1.7 g, 4.0 mmol) in DMF (50 mL) was added 60% sodium hydride (0.19 g, 4.9 mmol) under ice cooling, and the resulting solution was stirred for 35 minutes at the same temperature. 2-Bromoethylmethyl ether (0.4 mL, 4.2 mmol) was added dropwise to the solution. The reaction solution was stirred for 2 hours under ice cooling, and then stirred for 2 days at room temperature. To the reaction solution was added water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1), to thereby yield 1.6 g of the title compound.

Workup

  1. stirringThe reaction solution was stirred for 2 hours under ice cooling
  2. stirringstirred for 2 days at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-ba451cec932840daa7f657bc9c1249be
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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