Sodium hydride → Ethyl 2-[7-acetyl-7-(p-toluoylamino)heptyloxy]-2-methylpropionate

HRID 857246Notes

Reaction equation

HRID 857246 reaction equation
[H-].[Na+].[C:3]1([CH3:16])[CH:8]=[CH:7][C:6]([C:9]([NH:11][CH2:12][C:13](=[O:15])[CH3:14])=[O:10])=[CH:5][CH:4]=1.I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]([CH3:32])([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C)C=O>[C:13]([CH:12]([NH:11][C:9]([C:6]1[CH:5]=[CH:4][C:3]([CH3:16])=[CH:8][CH:7]=1)=[O:10])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]([CH3:31])([CH3:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21866667Ethyl 2-(6-iodohexyloxy)-2-methylpropionateHCID 218667451-(p-Toluoylamino)-2-propanone

Product 1

HCID 21866665Ethyl 2-[7-acetyl-7-(p-toluoylamino)heptyloxy]-2-methylpropionateYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A suspension (70 ml) of 1.81 g of 60% sodium hydride in N,N-dimethylformamide was cooled to −18° C. with ice-sodium chloride bath, and 21 ml of a solution of 8.67 g of 1-(p-toluoylamino)-2-propanone in N,N-dimethylformamide was added slowly. After 1-hour-stirring, 21 ml of a solution of 14.10 g of ethyl 2-(6-iodohexyloxy)-2-methylpropionate in N,N-dimethylformamide was added dropwise slowly. The bath was removed and the mixture was stirred for additional 18 hours at room temperature. The reaction solution was, after addition of ice-cold water, extracted with ethyl acetate, washed with water and brine sequentially, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=3:1) to provide 12.20 g of the objective compound as yellow crystals.

Workup

  1. customThe bath was removed
  2. stirringthe mixture was stirred for additional 18 hours at room temperature
  3. additionafter addition of ice-cold water
  4. extractionextracted with ethyl acetate
  5. washwashed with water and brine sequentially
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=3:1)

Sources & evidence

ORD record
ord-99cea394120844bfb16497583260d0a2
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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