Trifluoroacetic acid → HCID 59238164, compound

Participants

Reaction Steps

4-[3-(2-tert-butoxy-1-tert-butoxycarbonyl-ethyl)-4-oxo-3,4-dihydro-quinazolin-6-yl]-piperazine-1-carboxylic acid tert-butyl ester (4.7 g) was dissolved in anisole (8 mL) and cooled in an ice-water bath. Trifluoroacetic acid (80 mL) is added slowly. The mixture was stirred for 5 minutes while cooling with the ice-water bath and then for 5 hours at room temperature; during this time, the color of the reaction mixture changed from orange to red to purple to dark blue over time. At this time, the reaction solvents were removed in vacuo, leaving a blue oil. This oil was triturated with dry diethyl ether and evaporated to dryness again. The residue was again triturated with dry diethyl ether and stirred overnight with this solvent. At this time, the mixture was filtered and the resulting solid was washed with diethyl ether and dried in a vacuum oven, resulting in 4.4 g of a solid. This solid was used in the next step without further purification. H1-NMR spectroscopy indicated a spectrum consistent with 3-hydroxy-2-(4-oxo-6-piperazin-1-yl-4H-quinazolin-3-yl)-propionic acid.

Provenance & Evidence