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

HRID 1725567노트

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HRID 1725567 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6ef57c5c0c9446d1998d0127978d4ee3
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491728B2

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