Diisopropylethylamine → N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]-amino}propyl]-1-oxo-2-(1-propylbutyl)-1,2-dihydroisoquinoline-5-carboxamide

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Reaction Steps

77 mg of 1-oxo-2-(1-propylbutyl)-1,2-dihydroisoquinoline-5-carboxylic acid are dissolved in 4.5 cm3 of dichloromethane under an inert atmosphere at a temperature close to 20° C. 110 mg of (2R,3S)-3-amino-4-phenyl-1-{[3-(trifluoromethyl)benzyl]amino}butan-2-ol hydrochloride (1:1), 5 mg of hydroxybenzotriazole, 61 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added to the solution. 0.22 cm3 of N,N-diisopropylethylamine is poured into the reaction medium. The latter is kept stirring for 20 h at ambient temperature. 10 cm3 of water are added to the reaction medium. The organic phase is washed with 5 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 crude product obtained is purified by flash chromatography over silica (column: 15 g; particle size: 20-40 μm, spherical; flow rate: 20 cm3/min; eluent: 100% ethyl acetate). After concentrating the fractions under reduced pressure, 84 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-1-oxo-2-(1-propylbutyl)-1,2-dihydroisoquinoline-5-carboxamide are obtained in the form of a white solid.

Provenance & Evidence