Hydroxylamine → HCID 136054467, compound

Participants

Reaction Steps

To a solution of 4-{[3-({[(4-oxo-3,4-dihydroquinazolin-2-yl)carbonyl]amino}methyl)phenyl]oxy}butanoic acid obtained in Reference Example 44 (90.0 mg, 0.236 mmol) in THF (2 mL) were added DMF (0.02 mL) and oxalyl chloride (59.9 mg, 0.472 mmol) at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added a mixed solution of 50% aqueous hydroxylamine solution (0.5 mL), tert-butanol (0.5 mL) and THF (0.5 mL) at 0° C., and the mixture was stirred for 15 min. The mixture was concentrated under reduced pressure, and the residue was purified by preparative HPLC (GILSON 215LIQUD HANDLER, 322PUMP, UV/VIS-156, SHISEIDO CAPCELL PACK C-18 UG120 S-5 (20 mmφ×50 mm), mobile phase: distilled water (containing 0.1% trifluoroacetic acid)/acetonitrile (containing 0.1% trifluoroacetic acid), gradient: distilled water/acetonitrile=90/100/100, time: 10 min, flow rate: 25 mL/min, detection wavelength: 220 nm) to give a yellow powder. The obtained powder was recrystallized from ethyl acetate-hexane to give the title compound as a pale-yellow powder (8.0 mg, 9%).

Provenance & Evidence