Reaktion #485725

Reaktionsgleichung

2-aminothiazole

N-bromosuccinimide

triphenylphosphine

2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid

→

2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide

Ausbeute 88.3%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   workup.STIRRINGwas stirred at 0° C. for 5 min
3. 3
   Temperaturto warm to 25° C. where it
4. 4
   workup.STIRRINGwas stirred for 25 min
5. 5
   SonstigeThe resulting reaction mixture
6. 6
   workup.STIRRINGwas stirred at 25° C. for 15 h
7. 7
   SonstigeThe crude reaction mixture
8. 8
   Sonstigewas then directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate)

Vorschrift

A solution of triphenylphosphine (168 mg, 0.64 mmol) in methylene chloride (3 mL) was cooled to 0° C. and then slowly treated with N-bromosuccinimide (114 mg, 0.64 mmol). The reaction mixture was stirred at 0° C. for 10 min and then treated with 2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (200 mg, 0.53 mmol). The resulting reaction mixture was stirred at 0° C. for 5 min and then allowed to warm to 25° C. where it was stirred for 25 min. The reaction mixture was then treated with 2-aminothiazole (117 mg, 1.17 mmol). The resulting reaction mixture was stirred at 25° C. for 15 h. The crude reaction mixture was then directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) to afford 2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide (214 mg, 88%) as a yellow solid: mp 106-107° C.; EI-HRMS m/e calcd for C18H21BrN2O3S2 (M+) 456.0177, found 456.0175.

Quelle