Trifluoroacetic acid → HCID 178496721, compound

Participants

Reaction Steps

To a solution of 47.3 mg (50 μmol) of 16-({[5-(aminomethyl)-4-hydroxy-3-methoxytetrahydro-2-furanyl]oxy}{5-[2,4-dioxo-3,4-dihydro-1 (2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl)-9-(1-hydroxy-2-methylpropyl)-6-(2-iminohexahydro-4-pyrimidinyl)-2-isopropyl-4,7,10-trioxo-3,5,8,11, 15-pentaazaheptadecane-1,17-dioic acid λmax nm in water=259) in 2.5 ml of methanol is added 200 μl of pyridine and 200 μl of 2,4-pentanedione at room temperature. The reaction mixture is stirred overnight (the reaction is monitored by mass spectroscopy (MS)). After the reaction is complete, the volatile materials are removed under reduced pressure. N,N-dimethylformamide (DMF) (3 ml) is added to the residue, followed by addition of 13.0 mg (95 μmol) of 4-fluorophenyl isocyanate. The reaction mixture is stirred at room temperature for 50 hours (the reaction was monitored by MS). The volatile materials are removed under reduced pressure to afford a residue to which is added 5 ml of 0.5% trifluoroacetic acid (TFA) in a 1:1 mixture of water and p-dioxane. The mixture is stirred at room temperature for 2 hours. The reaction is monitored by MS and the desired product is identified by liquid chromatography/mass spectrum (LC/MS). After concentration of volatiles to about one ml, 24 mg (44% yield) of the desired product is obtained as a colorless solid using preparative high pressure liquid chromatography (HPLC).

Provenance & Evidence