1-(1H-Imidazol-1-yl)ethanone → HCID 19348510, compound

HRID 1637472Notes

Reaction equation

HRID 1637472 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[NH2:22])=[CH:17][C:16]=1[NH:24][C:25](=[O:41])[CH2:26][CH:27]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[O:39][CH3:40])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])([CH3:14])([CH3:13])[CH3:12].[C:42](N1C=CN=C1)(=[O:44])[CH3:43]>C1(C)C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[NH:22][C:42](=[O:44])[CH3:43])=[CH:17][C:16]=1[NH:24][C:25](=[O:41])[CH2:26][CH:27]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[O:39][CH3:40])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])([CH3:12])([CH3:13])[CH3:14]

Participants

7

Reactant 3

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 19348416HCID 19348416, compound

Product 1

HCID 19348510HCID 19348510, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.39 ml (1.19 mmol) of a 0.5 M potassium bis(trimethylsilyl)amide solution in toluene were added dropwise at room temperature over a period of 3 minutes to a solution of 338 mg (0.78 mmol) of N-(2-t-butyl-5-carbamoylphenyl)-3-(2-methoxyphenyl)octanamide (prepared as described in Example 151) in 5.0 ml of dry tetrahydrofuran, and the resulting mixture was stirred for 15 minutes, after which 175 mg (1.59 mmol) of 1-acetylimidazole were added. The reaction mixture was stirred for 40 minutes, after which it was diluted with ethyl acetate, and the diluted solution was washed with a saturated aqueous solution of potassium hydrogensulfate and with a saturated aqueous solution of sodium chloride, in that order. It was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 363 mg (a quantitative yield) of the title compound as a colorless foam-like substance.

Workup

  1. stirringThe reaction mixture was stirred for 40 minutes
  2. washthe diluted solution was washed with a saturated aqueous solution of potassium hydrogensulfate and with a saturated aqueous solution of sodium chloride, in that order
  3. dry with materialIt was then dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel using a 1:1
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-1ecda8529b6d473fbbbedb660e8731c4
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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