Reaktion #8632

Reaktionsgleichung

2-acetylamino-N-[2-[2-(1-benzyl-1H-imidazol-4-ylmethyl)-5-naphthalen-2-ylmethyl-3-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)propionamide

Cyclohexene

cyclohexene

→

desired product

2-acetylamino-N-{1-(4-fluorobenzyl)-2-[2-(1H-imidazol-4-ylmethyl)-5-naphthalen-2-ylmethyl-3-oxo-piperazin-1-yl]-2-oxo-ethyl]-3-(4-hydroxyphenyl)propionamide

Lösungsmittel

ethanol acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis cooled
2. 2
   Filtrationfiltered through Celite
3. 3
   Sonstigeto remove the catalyst
4. 4
   EinengenThe filtrate is concentrated in vacuo
5. 5
   Sonstigeto afford an oil which
6. 6
   Sonstigeis purified by reverse phase C18 prep HPLC

Vorschrift

2-acetylamino-N-[2-[2-(1-benzyl-1H-imidazol-4-ylmethyl)-5-naphthalen-2-ylmethyl-3-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)propionamide, 73, (0.22 g, 0.28 mmol) is dissolved in ethanol/acetic acid (4:1) (3 mL). Cyclohexene (3 mL) and Pd-black are added and the solution is refluxed with periodic replenishment of cyclohexene. The reaction is monitored by TLC and after 2 days is cooled and filtered through Celite to remove the catalyst. The filtrate is concentrated in vacuo to afford an oil which is purified by reverse phase C18 prep HPLC to afford the desired product.

Quelle