Reaktion #2178364

Reaktionsgleichung

β-alanine ethyl ester hydrochloride

1-hydroxybenzotriazole monohydrate

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

4-{[2-ethyl-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)butyl]amino}benzoic acid

Hydrochloric acid

→

compound

Ausbeute 27.0%

ethyl 3-{[(4-{[2-ethyl-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)butyl]amino}phenyl)carbonyl]amino}propanoate

Ausbeute 27.0%

Lösungsmittel

N,N-dimethylformamide

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto quench
2. 2
   Sonstigethe reaction
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe residue was purified by silica gel column chromatography (55% ethyl acetate/hexane)

Vorschrift

To a mixture of 4-{[2-ethyl-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)butyl]amino}benzoic acid (250 mg) synthesized above, β-alanine ethyl ester hydrochloride (151 mg), 1-hydroxybenzotriazole monohydrate (151 mg), triethylamine (275 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (188 mg), and the mixture was stirred at room temperature for 1 day. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (55% ethyl acetate/hexane) to give the title object compound (85.0 mg, 27%) as a pale-yellow oil.

Quelle