Water → 2-methyl-3-oxo-N-phenethyl-butyramide

HRID 1725567Notes

Reaction equation

HRID 1725567 reaction equation
[CH3:1][C:2]1([CH:7]([CH3:19])[C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:9])OCC[O:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH3:19][CH:7]([C:2](=[O:3])[CH3:1])[C:8]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 58921891HCID 58921891, compound

Product 1

HCID 119843462-methyl-3-oxo-N-phenethyl-butyramideYield 52%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(2-Methyl-[1,3]dioxolan-2-yl)-N-phenethyl-propionamide of Example 1c (0.40 g, 1.5 mmol) was added to p-toluenesulfonic acid monohydrate (0.48 g, 2.5 mmol) in water (20 mmol) under a nitrogen atmosphere at room temperature. Acetone (20 mL) was added, and the reaction mixture was stirred overnight at room temperature and then heated at 95° C. for 3 h. After cooling to room temperature, the solution was made basic with sodium carbonate (0.5 g). The acetone was removed at room temperature under vacuum and the remaining aqueous material was extracted with dichloromethane (50 mL). The organic layer was washed with water (50 mL), brine (50 mL) and then dried with sodium sulfate. After concentration, the product was purified by crystallization from hexanes-ethyl acetate (1:1) to give 2-methyl-3-oxo-N-phenethyl-butyramide (0.17 g, 52%) as a white solid.

Workup

  1. temperatureheated at 95° C. for 3 h
  2. temperatureAfter cooling to room temperature
  3. customThe acetone was removed at room temperature under vacuum
  4. extractionthe remaining aqueous material was extracted with dichloromethane (50 mL)
  5. washThe organic layer was washed with water (50 mL), brine (50 mL)
  6. dry with materialdried with sodium sulfate
  7. concentrationAfter concentration
  8. customthe product was purified by crystallization from hexanes-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-6ef57c5c0c9446d1998d0127978d4ee3
Source dataset
uspto-grants-2009_02
Patent number
US07491728B2

Reaction notes

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