Water → HCID 66701588, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (3-{[(1-allylcyclopropyl)sulfonyl]amino}-1-methyl-6-oxo-1,6-dihydropyridin-2-yl)(2-fluoro-4-iodophenyl)carbamate (180 mg, 0.298 mmol) in acetone (20 ml) was added water (3 ml). The mixture was cooled to 0° C. and 4-methylmorpholine N-Oxide (7.36 eq, 257 mg, 2.195 mmol) was added, followed by OsO4 (2.5% w.t. in t-butanole, 111 μl). The mixture was stirred a room temperature for 18 hours. Since the reaction was not complete, more 4-methylmorpholine N-Oxide (6 eq, 210 mg, 1.790 mmol) was added, followed by OsO4 (2.5% w.t. in t-butanole, 110 μl). The mixture was stirred a room temperature for another 18 hours and then concentrated in vacuo. The residue was diluted in ethyl methyl ketone and washed with water. The aqueouse phase was separated and extracted twice with ethyl methyl ketone. The combined organic layers were washed once with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound (177 mg, 93%).

Provenance & Evidence