Chloroform → HCID 69652407, compound

Participants

Reaction Steps

Add benzoyl chloride (0.11 mL, 0.98 mmol) to a solution of 3-aminomethyl-5-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.4 g, 0.89 mmol) in CH2Cl2 (10 mL). Add Et3N (0.4 mL, 2.67 mmol) and DMAP (5 mg, cat.). Stir 4 H at room temperature then add CHCl3. Wash 2× with sat. aq NaHCO3, wash 2× with 1N HCl, wash 2× with brine, dry over Na2SO4, filter and concentrate to dryness. Purify by radial chromatography using a MeOH/CHCl3 gradient as eluant. Purify again via radial chromatography using an EtOAc/hexane gradient as eluant and concentrate to dryness to afford the title compound (0.258 g, 53%) as a white foam as a mixture of cis isomers. MS(IS) 551.3 (M+). Purify via chiral HPLC (Chiralcel OD 4.6×250 mm. Eluant: 35% IPA, 65% heptane. Flow: 1.0 mL/min. UV: 240 nM). Chromatography affords isomer 1 of the title compound (59 mg, 23%) as a white solid. MS(IS) 551.3 (M+); Rt=7.0 min. Chromatography affords isomer 2 of the title compound (124 mg, 48%) as a white solid. MS(IS) 551.3; Rt=15.0 min.

Provenance & Evidence