Ozone → HCID 86728124, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl N-[(5R)-6-allyl-5-(2-fluoro-5-nitro-phenyl)-2,2,5,6-tetramethyl-1,1-dioxo-1,4-thiazin-3-yl]-N-tert-butoxycarbonyl-carbamate (0.18 g, 0.31 mmol) in DCM (2.4 ml) and MeOH (0.8 ml) was added sodium bicarbonate (0.053 g, 0.63 mmol) and then cooled in dry ice-acetone bath. A mixture of O3 in oxygen gas was bubbled through the solution until the blue color persisted. The excess ozone was removed by bubbling through oxygen gas for 5 minutes. Sodium borohydride (0.018 g, 0.47 mmol) was added and the mixture was stirred and allowed to warm to 0° C. After 30 minutes, the reaction was quenched by sat.NH4Cl and extracted with DCM. The combined extracts were washed with brine, dried and concentrated to give crude tert-butyl N-tert-butoxycarbonyl-N-[(5R)-5-(2-fluoro-5-nitro-phenyl)-6-(2-hydroxyethyl)-2,2,5,6-tetramethyl-1,1-dioxo-1,4-thiazin-3-yl]carbamate as a white solid. m/z (ESI) 611.0 (M+Na)+.

Provenance & Evidence