Reaktion #11708

Reaktionsgleichung

(2-{3-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-3-oxo-propyl}-5-methyl-phenoxy)-acetic acid

(3-(dimethylamino)propyl)ethyl carbodiimide hydrochloride

methanesulfonamide

triethylamine

→

title compound

Ausbeute 80.2%

N-[(2-{3-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-3-oxo-propyl}-5-methyl-phenoxy)-acetyl]-methanesulfonamide

Ausbeute 80.2%

Lösungsmittel

dichloromethane

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 0.2 M aqueous hydrochloric acid
2. 2
   TrocknenThe organic layer was dried over magnesium sulfate
3. 3
   Einengenconcentrated in vacuo
4. 4
   SonstigeThe crude product was purified by trituration in methylene chloride/diethyl ether/hexanes

Vorschrift

To a solution of (2-{3-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-3-oxo-propyl}-5-methyl-phenoxy)-acetic acid (0.052 g, 0.12 mmol) in methylene chloride (1 mL) was added 4-dimethylaminopyridine (0.022 g, 0.18 mmol), (3-(dimethylamino)propyl)ethyl carbodiimide hydrochloride (0.032 g, 0.17 mmol), methanesulfonamide (0.015 g, 0.16 mmol) and triethylamine (0.035 mL, 0.25 mmol). The reaction was stirred at ambient temperature for 18 hours. The reaction mixture was then diluted with dichloromethane and washed with 0.2 M aqueous hydrochloric acid. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by trituration in methylene chloride/diethyl ether/hexanes to give the title compound (0.050 g, LRMS: 520.3).

Quelle