Benzyl Bromide → HCID 131729222, compound

HRID 1662679Notes

Reaction equation

HRID 1662679 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:9]([N:11]([CH3:13])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:17][CH:16]=1)[C:9]([N:11]([CH3:12])[CH3:13])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 53913110HCID 53913110, compound

Product 1

HCID 131729222HCID 131729222, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.62 g of the compound obtained in Step 86-1 in DMF (30 ml) was added sequentially 1.29 g of K2CO3 and benzyl bromide (1.1 ml), and the reaction mixture was stirred at room temperature for 3 hours. The solution was cooled on ice, then, a saturated aqueous solution of NaHCO3 was added, and the mixture was extracted with EtOAc. The combined organic layer was washed with water and saturated brine, dried over MgSO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: n-hexane/EtOAc=1/1; v/v) to obtain 2.36 g of the title compound (colorless oil).

Workup

  1. temperatureThe solution was cooled on ice
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic layer was washed with water and saturated brine
  4. dry with materialdried over MgSO4
  5. customthe drying agent was separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: n-hexane/EtOAc=1/1; v/v)

Sources & evidence

ORD record
ord-72b27cf11ca8485bbb60221b6393cc6f
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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