Sodium Sulfite → HCID 89601340, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-acetamido-6-(1-hydroxyethyl)-3-oxo-5H-1,2,4-triazine-2-carboxylate (601 mg, 1.50 mmol) in ethyl acetate (3.9 mL) was added a solution of NaHCO3 (378 mg, 4.50 mmol) and NaBr (170 mg, 1.65 mmol) in water (2.6 mL). After cooling of the biphasic mixture to 0° C., 2,2,6,6-Tetramethyl-piperidin-1-yl)oxyl (“TEMPO”) (12.0 mg, 0.0750 mmol) was added in one portion followed by dropwise addition of NaOCl (6 wt % in water, 2.79 mL, 2.25 mmol) to the vigorously stirred solution. After completion of the addition, stirring at 0° C. was continued for 30 min. Subsequently, a solution of aqueous Na2SO3 was added until the reaction mixture had completely discolored. Additional solid Na2SO3 was added to saturate the aqueous phase. The mixture was transferred to a separation funnel and the layers were separated. The organic layer was washed with brine (100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. LCMS (Method I) RT 1.42 min. [(M-Boc)+Na]+ 221.

Provenance & Evidence