Réaction #171460

Équation de réaction

2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

1-hydroxy benzotriazole monohydrate

triethyl amine

O-tetrahydro-2H-pyran-2-yl-hydroxylamine

→

2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

1. 1
   Lavagewashed successively with sat.aqueous sodium bicarbonate, aqueous HCl (1 N) and water
2. 2
   SéchageThe organic extracts were dried over magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated to a crude residue
5. 5
   AutreThe crude residue was purified via silica gel chromatography
6. 6
   Lavageeluting with methylene chloride and methanol
7. 7
   workup.ADDITIONThe fractions containing the desired product
8. 8
   Concentrationconcentrated

Mode opératoire

To a solution of 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)butanoic acid (109.4 mg, 0.301 mmol) in methylene chloride (3 mL) at ambient temperature was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (80.7 mg, 0.421 mmol), 1-hydroxy benzotriazole monohydrate (83 mg, 0.542 mmol), triethyl amine (75 uL, 0.542 mmol) and O-tetrahydro-2H-pyran-2-yl-hydroxylamine (53 mg, 0.452 mmol). The resulting mixture was stirred at ambient temperature overnight. The mixture was diluted with methylene chloride and washed successively with sat.aqueous sodium bicarbonate, aqueous HCl (1 N) and water. The organic extracts were dried over magnesium sulfate, filtered and concentrated to a crude residue. The crude residue was purified via silica gel chromatography eluting with methylene chloride and methanol. The fractions containing the desired product were combined and concentrated to afford 2-methyl-4-(3-methyl-2-oxo-4-phenylpyridin-1(2H)-yl)-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide as a solid. 137.3 mg

Source