Sodium hydride → Ethyl 7-acetyl-7-(p-toluoylamino)heptanoate

HRID 890668Notes

Reaction equation

HRID 890668 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][C:23]([O:25][CH2:26][CH3:27])=[O:24]>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][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10880140Ethyl 6-iodohexanoateHCID 218667451-(p-Toluoylamino)-2-propanone

Product 1

HCID 21866896Ethyl 7-acetyl-7-(p-toluoylamino)heptanoateYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A suspension (100 ml) of 60% sodium hydride (2.64 g) in N,N-dimethylformamide was cooled to −18° C. with an ice-sodium chloride bath, and 31 ml of a solution of 12.62 g of 1-(p-toluoylamino)-2-propanone in N,N-dimethylformamide was added dropwise slowly. After 1-hour-stirring, 31 ml of a solution of 16.21 g of ethyl 6-iodohexanoate in N,N-dimethylformamide was added dropwise slowly. The ice-bath was removed and the mixture was stirred for 18 hours at room temperature. After addition of ice-cold water, the reaction solution was 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 13.13 g of the objective compound as yellow oil.

Workup

  1. customThe ice-bath was removed
  2. stirringthe mixture was stirred for 18 hours at room temperature
  3. additionAfter addition of ice-cold water
  4. extractionthe reaction solution was extracted 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-571d5c2090bc4214a9ac77abd0d5b466
Source dataset
uspto-grants-2006_02
Patent number
US06998412B2

Reaction notes

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