Hydrochloric Acid → HCID 67188665, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) solution of ethyl{(4-aminobenzyl)[4-(trifluoromethyl)benzyl]amino}-(oxo)acetate (140 mg, 0.37 mmol) in anhydrous pyridine (2 mL) was added (9Z)-tetradec-9-enoyl chloride (100 mg, 0.40 mmol) under inert atmosphere. The resulting reaction mixture was stirred for 1 h at 0° C. A 5 N aqueous solution of HCl (10 mL) was added and the mixture was extracted with Et2O (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to give a yellow oil. This crude product was purified by SPE (NH2 Isolute column) to give the title compound as a pale yellow oil (191 mg, 88%). 1H NMR (CDCl3, 300 MHz) δ 7.62 (m, 2H), 7.52 (m, 2H), 7.39 (d, 1H, J=8.0 Hz), 7.33 (d, 1H, J=7.9 Hz), 7.20 (m, 3H), 5.36 (m, 2H), 4.52 (s, 1H), 4.46 (s, 1H), 4.42-4.30 (m, 4H), 2.37 (t, 2H, J=7.5 Hz), 2.03 (m, 4H), 1.74 (m, 2H), 1.39-1.29 (m, 15H), 0.90 (t, 3H, 3=6.9 Hz). M−(LC/MS(ESI)): 587; M+(LC/MS(ESI)): 589. HPLC (Condition A), Rt: 7.24 min (HPLC purity: 97.3%).

Provenance & Evidence