1,2-Dichloroethane → 1-(t-Butoxycarbonyl)-cis-3-methoxycarbonyl-5-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-yl)acetylamino]-piperidine

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Reaction Steps

1-(t-Butoxycarbonyl)-cis-3-methoxycarbonyl-5-amino piperidine (134 mg, 0.520 mmol), [1-(4-cyanobenzyl)-1H-imidazol-5-yl]acetic acid (147 mg, 0.520 mmol), HOBT (73,8 mg, 0.546 mmol), EDC (104 mg, 0.546 mmol), and Et3N (65.2 uL, 0.468 mmol) were dissolved in DMF (4 mL) and stirred at ambient temperature overnight. The solution was concentrated under reduced pressure and the residue was chromatographed (silica gel, 0.5-2% MeOH/CH2Cl2 with NH4OH) to give the title compound. 1H NMR (CDCl3) d 7.64 (d, 2H, J=8 Hz), 7.52 (s, 1H), 7.19 (d, 2H, J=8 Hz), 6.90-7.05 (m, 1H), 6.98 (s, 1H), 5.22-5.35 (m, 2H), 3.78-3.91 (m, 2H), 3.69 (s, 3H), 3,57-3.64 (m, 1H), 3.45-3.56 (m, 1H), 3.34 (s, 2H), 3.05-3.30 (m, 1H), 2.55-2.68 (m, 1H), 2.05-2.13 (m, 1H), 1.55-1.70 (m, 1H), 1.42 (s, 9H). FAB MS 482 (M+1)

Provenance & Evidence