Ethyl Acetate → HCID 86673526, compound

Participants

Reaction Steps

To a solution of acid Boc-Ala-Lys-OH, (21) (207 mg, 0.5 mmol) in CH2Cl2 (5 mL) at 0° C., was sequentially treated with HOBt (101 mg, 0.75 mmol) and DCC (154 mg, 0.75 mmol). After 15 min., 4-((perfluoropyridin-4-yl)ethynyl)aniline (7) (154 mg, 0.08 mmol) was added to the reaction mixture. After stirring for 1 days at room temperature, the reaction mixture was diluted with ethylacetate, washed with saturated NH4Cl solution, saturated NaHCO3, 1 N HCl, water, brine, dried (Na2SO4), filtered and concentrated in vacuo. Chromatographic purification (SiO2, 50% ethylacetate in hexane) of the residue provided (22) (170 mg, 52%) as a white solid; 1H NMR (400 MHz, CD3OD): 1H NMR (400 MHz, CDCl3): δ 9.17 (bs, 1H), 7.72 (d, J=8.5 Hz, 2H), 7.53 (d, J=8.5 Hz, 2H), 6.91 (bs, 1H), 5.22 (bs, 1H) , 4.75 (bs, 1H) , 4.57 (bs, 1H) , 4.21-4.12 (m, 1H), 3.17-3.05 (m, 2H), 1.81-1.62 (m, 2H), 1.61-1.31 (m, 25H); MS (ESI): m/z (%) 688 (100) [M+Na]+;

Provenance & Evidence