Dimethylformamide → tert-butyl ((4aRS,11bRS)-3,3,11b-trimethyl-10-nitro-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate

Participants

Reaction Steps

To a solution of tert-butyl ((5RS,6RS)-5-(2-fluoro-5-nitrophenyl)-6-(2-hydroxyethyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)carbamate (120 mg, 0.253 mmol) in the mixture of THF (2 ml) and DMF (0.2 ml) sodium hydride (60% dispersion in mineral oil) (25.3 mg, 0.634 mmol) was added and the mixture was stirred for 10 min at RT. The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOAc. The organic layer was washed with brine and concentrated. The residue was purified by FC on 12 g RediSep Gold column using 10-100% EtOAc/heptane to afford tert-butyl ((4aRS,11bRS)-3,3,11b-trimethyl-10-nitro-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (100 mg, 0.221 mmol, 87% yield).

Provenance & Evidence