Potassium Bromide → HCID 67951276, compound

Participants

Reaction Steps

To a solution of (3S)-tert-butyl 3-amino-3-(4-(2-fluoro-3-(hydroxymethyl)pyridin-4-yl)-3-methylisoxazol-5-yl)propanoate (200 mg, 0.569 mmol) and TEMPO (4.45 mg, 0.028 mmol) in CH2Cl2 (5 mL) at 0° C. was sequentially added potassium bromide (33.9 mg, 0.285 mmol) and an aqueous solution of sodium hypochlorite (˜0.35M buffered to pH ˜8.6 with sodium bicarbonate) (4.879 mL, 1.708 mmol). The reaction was vigorously stirred (to produce an emulsion) at 0° C. for 45 min before diluting with CH2Cl2. The product was extracted with CH2Cl2 (repeated once), with CH2Cl2/MeOH (95:5) (repeated once) and CH2Cl2/TFE (95:5) (repeated once). The organic layers were combined, dried over a cotton plug and concentrated to dryness under vacuum. The residue was purified by flash chromatography (Hexane/EtOAc 8:2 to 5:5) to give tert-butyl 2-((4S)-7-fluoro-1-methyl-6-oxo-5,6-dihydro-4H-isoxazolo[5,4-c]pyrido[4,3-e]azepin-4-yl)acetate as a solid (45 mg). LC/MS m/z 348 [M+H]+.

Provenance & Evidence