Reaktion #1054023

Reaktionsgleichung

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

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

triethylamine

2-aminoimidazole sulfate

→

2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(1H-imidazol-2-yl)-propionamide

Ausbeute 58.9%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was partitioned between water and methylene chloride
2. 2
   WaschenThe organic layer was washed sequentially with a 1N aqueous hydrochloric acid solution (1×10 mL) and water (1×10 mL)
3. 3
   TrocknenThe organic layer was dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo

Vorschrift

A solution of 2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (prepared as in Example 148A, 100 mg, 0.266 mmol), benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (187 mg, 0.42 mmol), triethylamine (115 μL, 1.064 mmol), and 2-aminoimidazole sulfate (56 mg, 0.42 mmol) in methylene chloride (10 mL) was stirred at 25° C. for 15 h. The reaction mixture was partitioned between water and methylene chloride. The organic layer was washed sequentially with a 1N aqueous hydrochloric acid solution (1×10 mL) and water (1×10 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, ethyl acetate) afforded 2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(1H-imidazol-2-yl)-propionamide (69 mg, 53%) as a white solid: mp >210° C. (dec); EI-HRMS m/e calcd for C18H22BrN3O3S(M+) 439.0565, found 439.0566.

Quelle