1-Hydroxybenzotriazole → (S)-1-(3-Fluoro-benzenesulfonyl)-piperidine-2-carboxylic acid [(S)-2-[4-(3-fluoro-propoxy)-phenyl]-1-((S)-2-methoxy-1-methyl-ethylcarbamoyl)-ethyl]-amide

Beteiligte Stoffe

Reaktionsschritte

(S)-2-{[1-(3-Fluoro-benzenesulfonyl)-piperidine-2-carbonyl]-amino}-3-[4-(3-fluoro-propoxy)-phenyl]-propionic acid (compound 18b) (80 mg, 0.16 mmol), (S)-1-methoxy-2-propylamine (14 mg, 0.16 mmol), 1-hydroxybenzotriazole (30 mg, 0.22 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (39 mg, 0.20 mmol) were mixed in dichloromethane (2 mL). The mixture was stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane, washed twice with a saturated aqueous sodium bicarbonate solution, and the organic layer was dried over magnesium sulfate. After manual filtration and subsequent concentration the resulting oil was chromatographed on silica gel (dichloromethane/methanol, 9/1) on silica gel to provide 66 mg (72%) of the title compound. MS: m/e 582.2 (M+H). 1H NMR (300 MHz, d6-DMSO): δ0.75-1.60 (m, 9H), 1.85-2.15 (m, 3H), 2.75 (m, 1H), 2.85 (m, 1H), 3.10 (m, 1H), 3.20 (m, 1H), 3.60 (d, 1H, J=12 Hz), 3.85 (m, 1H), 4.00 (t, 2H, J=6 Hz), 4.30 (q, 1H J=7.5 Hz), 4.50 (m, 2H), 4.65 (t, 1H, J=6 Hz), 6.85 (d, 2H, J=9 Hz), 7.15 (d, 2H, J=9 Hz), 7.40 (m, 4H), 7.75 (d, 1H, J=9 Hz), 7.90 (d, 1H, J=6 Hz).

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