Hydrogen Peroxide → HCID 58052401, compound

Participants

Reaction Steps

H2O2 (30%) (0.222 mL, 2.170 mmol) was added to a solution of 6-(N—((S)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentyl)methylsulfonamido)-5-cyclopropyl-N-methyl-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (365 mg, 0.543 mmol) in 6.4 mL of 7:3 THF/water at 0° C. Added LiOH (26.0 mg, 1.085 mmol) Stirred at 0° C. for 15 min. Quenched with sodium sulfite (342 mg, 2.71 mmol) in 2 mL water followed by sodium bicarbonate (0.5 M) (5.43 mL, 2.71 mmol) Added DCM and extracted AQ layer Treated AQ layer with 1N HCl and then extracted with EtOAc. Concentrated Chiral HPLC using a 20-250 mm IA column running 40% EtOH in heptane gave 294 mg (0.572 mmol) desired enantiomer at 9.4 min. and 120 mg of undesired enantiomer at 13.3 min. The desired enantiomer was taken up in 2 mL MeOH and salted with 0.5 N KHCO3 and lyophylized.

Provenance & Evidence