Water → HCID 15018294, compound

HRID 846584Notes

Reaction equation

HRID 846584 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH2:16][O:15][C:14](=[O:18])[NH:13][C:12]=3[N:11]=[C:10]([CH:19]([CH3:21])[CH3:20])[C:9]=2[CH:22]=[O:23])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C)C=O>[CH2:26]([N:13]1[C:12]2[N:11]=[C:10]([CH:19]([CH3:21])[CH3:20])[C:9]([CH:22]=[O:23])=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:17]=2[CH2:16][O:15][C:14]1=[O:18])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 15018290HCID 15018290, compound

Product 1

HCID 15018294HCID 15018294, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.36 g (7.5 mmol) of the compound from Example VII are dissolved in 20 ml of anhydrous dimethylformamide, and the mixture is treated with 0.28 g (9.4 mmol) of 80% strength sodium hydride under a gentle stream of argon. The mixture is stirred at room temperature for 15 min and treated with 1.54 g (9 mmol) of benzyl bromide. After 60 min, 30 ml of water are cautiously added and the mixture is extracted twice with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated to dryness in vacuo. The residue which remains is chromatographed in a column (φ 3 cm) on 50 g of silica gel 230-400 mesh using petroleum ether/ethyl acetate 4:1.

Workup

  1. waitAfter 60 min
  2. extractionthe mixture is extracted twice with ethyl acetate
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to dryness in vacuo
  6. customThe residue which remains is chromatographed in a column (φ 3 cm) on 50 g of silica gel 230-400 mesh

Sources & evidence

ORD record
ord-aa36ba15c5dd462a95adfed56bcd5c85
Source dataset
uspto-grants-1992_08
Patent number
US05137881

Reaction notes

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