Trifluoroacetic acid → HCID 24872067, compound

Participants

Reaction Steps

153 mg (0.203 mmol) TFA salt of (10) together with 150 mg (0.406 mmol) 2-(2,4,6-trimethylbenzoylamino)-3-(4-boronophenyl)propionic acid methyl ester (12), 844 μl (6.1 mmol) triethlamine and 74 mg (0.406 mmol) Cu(OAc)2 were stirred in 2.5 ml DCE for 20 min under ultrasonification and then stirring was continued for another 20 h at room temperature. The reaction mixture was filtered over a pad of Celite, the solvent was removed under reduced pressure and the residue was dissolved in acetonitrile to be filtered over another pad of Celtite. After the solvent was removed, the crude methyl ester was dissolved in 9 ml methanol and stirred with 4 ml 0.5 M NaOH over the weekend. Solids were removed by filtration and the reaction mixture was purified by reversed phase HPLC using a water/acetonitrile gradient containing 0.1% TFA yielding the TFA salt of (11) after lyophilization as a white powder.

Provenance & Evidence