Benzyl succinimido carbonate → Benzyl (1R,2R)-2-((S)-1-(4-(oxazol-2-yl)phenyl)piperidin-3-ylamino)cyclohexylcarbamate

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Reaction Steps

Benzyl (1R,2R)-2-((S)-1-(4-(oxazol-2-yl)phenyl)piperidin-3-ylamino)cyclohexylcarbamate was synthesized using (1R,2R)—N1-(1-(4-(oxazol-2-yl)phenyl)piperidin-3-yl)cyclohexane-1,2-diamine (from Example 15, step D) (11.58 mg, 0.034 mmol) and benzyl 2,5-dioxopyrrolidin-1-yl carbonate (8.5 mg, 0.034 mmol) according to General Procedure H to give 5 mg (20% yield) of the title compound as a pink solid. Anal. Calcd. for C28H34N4O3 m/z 474.5, found: 475.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.90 (d, J=8.8 Hz, 2H), 7.71 (s, 1H), 7.39 (s, 1H), 7.24-7.08 (m, 5H), 6.98 (d, J=8.7 Hz, 2H), 4.79 (s, 2H), 3.67-3.53 (m, 1H), 3.53-3.42 (m, 2H), 3.42-3.30 (m, 2H), 3.29-3.19 (m, 2H), 2.22 (d, J=10.4 Hz, 1H), 2.14-1.85 (m, 5H), 1.84-1.54 (m, 4H), 1.44-1.19 (m, 2H).

Provenance & Evidence