Diisopropylethylamine → (S)-5-[4-(3-Chloro-benzoyl)-piperidin-1-yl]-4-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-5-oxo-pentanoic acid

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Reaction Steps

To a solution of 150 mg (S)-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-pentanedioic acid 5-tert-butyl ester in 7 ml DMF were added 62 μl DIPEA, 95 mg HATU and 56 mg 4-(3-chlorobenzoyl)-piperidine. After stirring for 12 h saturated NaHCO3 solution was added and the mixture loaded on a Chem Elut® cartridge, the crude product being eluted with dichloromethane. The solution was concentrated to a volume of 1 ml and stirred in the presence of 100 μl TFA. After stirring for 4 h the solvents were removed under reduced pressure and the residue purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1% TFA). The fractions containing the product were lyophilized to yield the pure product. Yield: 135 mg MS (ES+): m/e=747.

Provenance & Evidence