Reaktion #2057618

Reaktionsgleichung

1-(3-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid

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

EDC

→

crude product

4-((S)-4-tert-Butoxycarbonyl-2-{[1-(3-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester

Lösungsmittel

DMF

DIPEA

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThen the reaction mixture was evaporated
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   Extraktionsubsequently extracted with aqueous LiCl (4% w/w) and aqueous NaHCO3
4. 4
   TrocknenThe organic layer was dried over MgSO4
5. 5
   Sonstigethe solvent was removed under reduced pressure

Vorschrift

To a solution of 2.500 g 1-(3-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid (prepared by standard procedure using 3-fluorophenylhydrazine hydrochloride and sodium diethyl-2-oxosuccinate followed by ester hydrolysis) and 3.864 g 4-((S)-2-amino-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid ethyl ester in 20 ml DMF 1.723 g HOBt, 1.9 ml DIPEA and 2.157 g EDC were added and the reaction mixture was stirred for 16 h at RT. Then the reaction mixture was evaporated, diluted with ethyl acetate and subsequently extracted with aqueous LiCl (4% w/w) and aqueous NaHCO3. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The crude product thus obtained was used in the subsequent reaction.

Quelle