Diisopropylethylamine → N-[(1S,2R)-1-Benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

136.4 mg of 1-oxo-2-(1-propylbutyl)isoindoline-4-carboxylic acid are dissolved in 8 cm3 of dichloromethane under an inert atmosphere at a temperature close to 20° C. 195 mg of ((2R,3S)-3-amino-4-phenyl-1-{[3-(trifluoromethyl)benzyl]amino}butan-2-ol hydrochloride (2:1), 9.6 mg of hydroxybenzotriazole, and 108.7 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added to the solution. 0.308 cm3 of N,N-diisopropylethylamine is poured into the reaction medium. This is kept stirring for 20 h at 20° C. 10 cm3 of water are added to the reaction medium. The organic phase is washed with 10 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated using a rotary evaporator under reduced pressure (5 kPa). The 310 mg of beige gum obtained are purified by flash chromatography over silica (column: 15 g; particle size: 20-40 μm, spherical; flow rate: 20 cm3/min; eluent: 95% dichloromethane/5% methanol). After concentrating the fractions under reduced pressure, 110 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)isoindoline-4-carboxamide are obtained in the form of a beige foam.

Provenance & Evidence