Triethylamine → HCID 67191334, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (50 μL) was added to a stirred suspension of (3R)-3-((S)-1-(3-bromophenyl)-1-hydroxy-5-methoxypentyl)-N—((S)-1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)piperidine-1-carboxamide (21.0 mg, 0.03 mmol), Pd(dppf)Cl2 (5 mg) and Pd(PPh3)4 (5 mg) in 4:1 DMF/MeOH (2 mL). A carbon monoxide atmosphere was established in the reaction vessel and the mixture was stirred at 70° C. overnight. After cooling to ambient temperature, the mixture was extracted with EtOAc (2×5 mL) and the combined organic layers were washed with 1 N aq HCl (2×1 mL) and concentrated. The residue was purified by preparative HPLC to give methyl 3-((S)-1-((R)-1-((S)-1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-ylcarbamoyl)-piperidin-3-yl)-1-hydroxy-5-methoxypentyl)benzoate (5.4 mg, 27%). MS m/z 698 (M+Na+).

Provenance & Evidence