Reaktion #641005

Reaktionsgleichung

4-((S)-2-amino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester

oxalyl chloride

6-chloro-2-phenyl-pyrimidine-4-carboxylic acid

NEt3

→

4-{(S)-4-tert-butoxycarbonyl-2-[(6-chloro-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester

Lösungsmittel

acetonitrile

acetonitrile

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 3 h
2. 2
   Extraktionthe reaction mixture was extracted with EA
3. 3
   Trocknenlayers were dried (Na2SO4)
4. 4
   Sonstigeevaporated off
5. 5
   SonstigePurification by column chromatography (EA/Hept 1/3 to 1/2)

Vorschrift

Under argon, oxalyl chloride (0.843 ml) was added to a solution of 6-chloro-2-phenyl-pyrimidine-4-carboxylic acid (1.17 g) in acetonitrile (50 ml) and it was refluxed for 3 h. The reaction mixture was cooled down to 0° C. and NEt3 (2.07 ml) was added, followed by 4-((S)-2-amino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester (1.7 g) in 10 ml acetonitrile. It was stirred at RT under argon for 1 h. Water was added and the reaction mixture was extracted with EA. The org. layers were dried (Na2SO4) and evaporated off. Purification by column chromatography (EA/Hept 1/3 to 1/2) offered 1.61 g of the desired compound.

Quelle