Reaktion #517377

Reaktionsgleichung

benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

3-cyclopentyl-2-(3,4-dichlorophenyl)-propionic acid

N,N-diisopropylethylamine

2-aminooxazole

→

3-cyclopentyl-2-(3,4-dichlorophenyl)-N-oxazol-2-yl-propionamide

Ausbeute 47.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was partitioned between water and ethyl acetate
2. 2
   WaschenThe organic layer was washed with a 1N aqueous hydrochloric acid solution
3. 3
   Waschenwashed with water
4. 4
   Waschenwashed with a saturated aqueous sodium chloride solution
5. 5
   TrocknenThe organic layer was dried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo

Vorschrift

A solution of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (102 mg, 0.23 mmol), 3-cyclopentyl-2-(3,4-dichlorophenyl)-propionic acid (prepared in Example 38, 60 mg, 0.21 mmol), N,N-diisopropylethylamine (73 μL, 0.42 mmol), and 2-aminooxazole (27 mg, 0.31 mmol) in dry N,N-dimethylformamide (1 mL) was stirred at 25° C. under nitrogen for 15 h. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with a 1N aqueous hydrochloric acid solution, washed with water, and washed with a saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(3,4-dichlorophenyl)-N-oxazol-2-yl-propionamide (34.9 mg, 47%) as a white solid: mp 134-136° C.; EI-HRMS m/e calcd for C17H18Cl2N2O2(M+) 352.0745, found 352.0750.

Quelle