Triethylamine → HCID 69652414, compound

Participants

Reaction Steps

Add HOAt (30 mg, 0.22 mmol), EDCI (41 mg, 0.22 mmol), Et3N (0.075 mL, 0.54 mmol), and DMAP (5 mg, cat.) to a solution of 5-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (83 mg, 0.18 mmol) in DMF (5 mL). Stir overnight at room temperature and concentrate to dryness. Dissolve in 20% iPrOH/CHCl3. Wash 2× sat. aq NaHCO3, wash 2× with brine, dry over Na2SO4, filter, and concentrate to dryness. Purify by radial chromatography using a MeOH/CHCl3 gradient as eluant and concentrate to dryness. Slurry the residue in ether/hexanes and concentrate to dryness to afford the title compound (44 mg, 50%) as a white foam as a mixture of cis isomers. MS(IS) 552.2 (M+); HPLC (100% EtOH 0.2% DMEA on a Chiralpak AD (0.46×25 cm) 1.0 mL/min flow; 20 μL Inj. Vol.; 225 nM) Rt=6.291 min (67.8%), 13.156 min (24.4%).

Provenance & Evidence