1,2-Dichloroethane → HCID 67587357, compound

Participants

Reaction Steps

N-(t-Butoxycarbonylpiperidin-2(S)-ylmethyl)-N-(1-naphthylmethyl)glycine (2.00 g, 5.0 mmol), dissolved in CH2Cl2 (50 mL), was treated with HOBT (0.743 g, 5.5 mmol), EDC (1.05 g, 5.5 mmol), and methionine methyl ester hydrochloride (1.20 g, 6.0 mmol). The pH was adjusted to 7.5 with Et3N (2.1 mL, 15 mmol) and the mixture was stirred at ambient temperature for 18 h. The mixture was diluted with EtOAc (50 mL), washed with 10% citric acid solution, water, and saturated NaHCO3 solution, brine and dried (MgSO4). Filtration and concentration gave the title compound. 1H NMR (CDCl3); δ8.21 (d, 1H, J=8 Hz), 7.87 (d, 1H, J=8 Hz), 7.80 (d, 1H, J=8 Hz), 7.35-7.6 (m, 5H), 4.33-4.5 (m, 2H), 3.85-4.05 (m, 2H), 3.26 (s, 3H), 3.15-3.33 (m, 2H), 2.62-2.96 (m, 1H), 2.53-2.65 (m, 1H), 2.17 (s, 3H), 1.78-2.05 (m, 4H), 1.15-1.72 (m, 8H), 1.48 (s. 9H).

Provenance & Evidence