Acetone → HCID 22019689, compound

HRID 7063Notes

Reaction equation

HRID 7063 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]([NH:13][C:14](=[O:26])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>O>[CH2:27]([O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:14]([NH:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:8]=2)=[O:26])=[CH:17][C:18]=1[N+:23]([O-:25])=[O:24])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22019622HCID 22019622, compound

Product 1

HCID 22019689HCID 22019689, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(3-cyclohexylphenyl)-4-hydroxy-3-nitrophenylacetamide (the compound of Example 29) (300 mg), benzyl bromide (287 mg), potassium carbonate (500 mg) and acetone (10 ml) is heated under reflux for 18 hours. After cooling, water is added to the mixture, and the mixture is extracted with ethyl acetate. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 4-benzyloxy-N-(3-cyclohexylphenyl)-3-nitrophenylacetamide (320 mg). This product is dissolved in ethanol (5 ml), and thereto are added reduced iron (200 mg), ammonium chloride (80 mg) and water (5 ml), and the mixture is heated under reflux for one hour. The reaction solution is filtered through Celite, and the filtrate is concentrated, and the residue is dissolved in chloroform. The organic layer is washed with water, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (240 mg).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. customthe solvent is evaporated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6f11a7e25767446b9f431cd76e2a0831
Source dataset
uspto-grants-2006_08
Patent number
US07084176B2

Reaction notes

Loading…