Potassium bis(trimethylsilyl)amide → HCID 69652406, compound

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Reaction Steps

Add KHMDS (1.6 mL, 0.80 mmol, 0.5 M in toluene) to a solution of 5-{[3-(2-chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (0.27 g, 0.53 mmol) in DMF (10 mL). After 5 min, quench with water and concentrate to dryness. Dissolve in 20% iPrOH/CHCl3. Wash 2× with sat. aq NaHCO3, wash 2× with brine, dry over Na2SO4, filter, and concentrate to dryness. Purify by radial chromatography using EtOAc/hexanes as eluant and concentrate to dryness to afford the title compound (94 mg, 35%) as a colorless oil as a mixture of cis isomers. MS(IS) 490.1 (M+); HPLC (100% EtOH on a Chiralpak AD (0.46×25 cm) 1.0 mL/min flow; 20 μL Inj. Vol.; 225 nM) Rt=5.688 min (66.3%), 6.462 min (22.9%).

Provenance & Evidence