Reaktion #2196190

Reaktionsgleichung

{4-[(2S)-2,3-diethoxy-3-oxopropyl]phenoxy}acetic acid

N-hexyl-benzylamine

1-ethyl-3-(3dimethylaminopropyl) carbodiimide hydrochloride

→

colourless oil

Ausbeute 80.0%

Ethyl(2S)-3-(4-{2-[benzyl(hexyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate

Ausbeute 80.0%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe organic phase was washed with 5% HCl (3×25 mL), aqueous NaHCO3 (25 mL), and brine (25 mL)
2. 2
   Trocknendried over Na2SO4
3. 3
   Einengenconcentrated in vacuo
4. 4
   SonstigePurification on a prepacked column of silica gel (Isolute® SPE Column, 5 g Si/25 mL) with methanol (0-1% gradient) in methylene chloride as the eluent

Vorschrift

To a solution of {4-[(2S)-2,3-diethoxy-3-oxopropyl]phenoxy}acetic acid (0.110 g, 0.37 mmol) in methylene chloride (3.7 mL) were added N-hexyl-benzylamine (0.079 g, 0.41 mmol) and DMAP (0.045 g, 0.37 mmol) followed by 1-ethyl-3-(3dimethylaminopropyl) carbodiimide hydrochloride (0.071 g, 0.37 mmol) and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with methylene chloride (25 mL), and the organic phase was washed with 5% HCl (3×25 mL), aqueous NaHCO3 (25 mL), and brine (25 mL), dried over Na2SO4, and concentrated in vacuo. Purification on a prepacked column of silica gel (Isolute® SPE Column, 5 g Si/25 mL) with methanol (0-1% gradient) in methylene chloride as the eluent yielded 0.139 g (80%) of a colourless oil.

Quelle