Sodium hydride → HCID 54288573, compound

HRID 2225808Notes

Reaction equation

HRID 2225808 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].[CH:16]1([NH:24][C:25](=[O:28])[CH2:26]Br)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:26][C:25]([NH:24][CH:16]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:28])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 190044022-Bromo-N-cyclooctylacetamide

Product 1

HCID 54288573HCID 54288573, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Bromoacetyl chloride (0.25 mL) was added slowly to a chilled (ice-water-bath) solution of cyclooctylamine (0.763g) in dichloromethane (15 mL) and the mixture was stirred with cooling for 45 minutes, then at room temperature overnight. After water (20 mL) was added, the layers were separated and the dried organic layer (MgSO4) was evaporated to provide 0.7 g of N-cycloocyl-bromoacetamide. A solution of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.605 g) in dimethylformamide (8 mL) under argon was treated with 55% sodium hydride (0.147 g), stirred for 30 minutes and then N-cyclooctyl-bromoacetamide (0.7 g) in dimethylformamide (5 mL) was added. The solution was stirred at room temperature for 18 hours and worked up as in Example 20. The crude material was purified by flash chromatography (ethyl acetate-hexane; 3:7) to yield 0.4 g of 4-[2-(cyclooctylamino)-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester as an oil.

Workup

  1. stirringThe solution was stirred at room temperature for 18 hours
  2. customThe crude material was purified by flash chromatography (ethyl acetate-hexane; 3:7)

Sources & evidence

ORD record
ord-1e303509778f4e74812ebedeced39728
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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