1,2-Dichloroethane → HCID 86584722, compound

Participants

Reaction Steps

A solution of O-(2,6-dichlorobenzyl)-L-tyrosine methyl ester hydrochloride, (1.11 g, 2.84 mmol), 2-chloronicotinic acid (0.45 g, 2.84 mmol), EDC (0.60 g, 3.13 mmol), HOBT (0.46 g, 3.41 mmol) and NMM (0.467 ml, 0.43 g, 4.26 mmol) in DCM (25 ml) was stirred at room temperature for 24 h. The reaction mixture was partitioned between DCM (50 ml) and 10% NaHCO3 solution (30 ml). The organic layer was separated, dried over MgSO4 and the solvent removed under vacuum to give a pale yellow solid that was recrystallized from EtOAc/hexane to give the title compound as an off white solid (1.14 g, 81%), δH (CDCl3) 8.46 (1H, dd, J 2.0, 4.7Hz), 8.05 (1H, dd, J 2.0, 7.6Hz), 7.34 (2H, m), 7.25 (2H, m), 7.11 (2H, m), 6.96 (3H, m), 5.24 (2H, s), 5.06 (1H, m), 3.80 (3H, s) and 3.24 (2H, m).

Provenance & Evidence