Acetate → HCID 20680718, compound

Participants

Reaction Conditions

Reaction Steps

[1-(4-chloroquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]carbamic acid tert-butyl ester (250 mg, 0.665 mmol), phenol (626 mg, 6.65 mmol), and anhydrous acetate (513 mg, 6.65 mmol) are combined and heated at 100° C., with reflux apparatus, under nitrogen overnight. Then the mixture is cooled to room temperature, and acetonitrile (20 mL) and water (20 mL) are added. The solution separates into 2 phases (both containing product), which are concentrated to dryness, and separately purified by reverse phase preparation HPLC with gradient elution 20-40% acetonitrile/water (0.1% trifluoroacetic acid). The product fractions from each run are combined, the solvents are removed in vacuo, and the residue dried under high vacuum overnight. The [1-(4-Aminoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]carbamic acid tert-butyl ester intermediate is dissolved in methanol, and cooled to 0° C., whilst bubbling dry HCl(g) through the solution until saturated. The reaction mixture is left at room temperature for 2 hours, and concentrated in vacuo. The residue is washed with ether to give the pure product as a colorless powder (170 mg, 0.516 mmol).

Provenance & Evidence