1,2-Dichloroethane → Coumarin

Participants

Reaction Steps

EDC (1.0 mg, 0.0052 mmol) and DMAP (0.64 mg, 0.0052 mmol) were added to a stirred solution of terpestacin (2.0 mg, 0.005 mmol) and Boc-6-aminohexanoic acid (1.2 mg, 0.0052 mmol) in DMF (2 mL) at 0° C. The reaction mixture was reacted overnight at room temperature. The reaction product was extracted with ethanol (4 mL×3), treated with 20% TFA in CH2Cl2 (1 mL) and stirred at room temperature for 2 hours. DIPEA (1.3 mg, 0.01 mmol) and 6-((7-amino-4-methylcoumarin-3-acetyl)amino)hexanoic acid succinimidyl ester (2.2 mg, 0.005 mmol, MOLECULAR PROBES®) were added thereto at 0° C. After being stirred at room temperature for 4 hours, the reaction product was extracted with ethanol (20 mL) and purified by TLC (CH2Cl2:MeOH=10:1) to obtain coumarin-conjugated terpestacin (yield: 61%). The synthesized coumarin-conjugated terpestacin is depicted in Formula 4.

Provenance & Evidence