Triethylamine → HCID 28347086, compound

HRID 2095829Notes

Reaction equation

HRID 2095829 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](Cl)=[O:17])=[CH:11][CH:10]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C(=O)C.C(OCC)(=O)C.O1CCCC1>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:2][CH2:3][CH2:4][C:5](=[O:7])[CH3:6])=[O:17])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 37449884-Fluorophenylacetyl chlorideHCID 155650274-Aminobutan-2-one hydrochloride

Product 1

HCID 28347086HCID 28347086, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

To a solution of 4-aminobutan-2-one hydrochloride (2.95 g, 24 mmol) in N,N-dimethylacetamide (50 mL) was slowly added (4-fluorophenyl)acetylchloride (4.90 g, 29 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. Triethylamine (4.80 g, 48 mmol) was added to the mixture, and the mixture was stirred at room temperature for 17 hr. Ethyl acetate/tetrahydrofuran and saturated aqueous sodium hydrogen carbonate solution were added to the mixture, and the aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3). The combined organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) to give the title compound (2.10 g, 39%) as a white solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 17 hr
  3. extractionthe aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3)
  4. washThe combined organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)

Sources & evidence

ORD record
ord-af0c0fe684af4b11a28e5ee78d574cca
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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