Ammonium Chloride → HCID 90308594, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-tert-butyl-N-(5-(2-(3-iodopropyl)-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)-N-tert-butoxycarbonyl-carbamate (172 mg, 0.253 mmol) in THF (2.5 ml) was cooled down to −78° C. and lithium bis(trimethylsilyl)amide (1M solution in THF) (0.40 ml, 0.40 mmol) was added dropwise. The bright yellow mixture was stirred at −78° C. for 20 min, then transferred to −45° C. bath (acetonitrile-dry ice) and stirred for extra 5 min. Saturated NH4Cl (2 ml) solution was added, the mixture was removed from the bath and allowed to reach rt, diluted with EtOAc (5 ml) and water to dissolve solids. Organic layer was washed with brine and concentrated. The residue was purified by FC on 12 g RediSep column using 20-70% EtOAc in heptane to afford tert-butyl-N-((4aS,11bR)-10-nitro-3,3,11b-trimethyl-4,4-dioxido-3,4a,5,6,7,11b-hexahydrobenzo[3,4]cyclohepta[1,2-b][1,4]thiazin-2-yl)-N-tert-butoxycarbonyl-carbamate (105 mg, 0.190 mmol, 75% yield) as white solid. LC/MS (ESI+) m/z=574 (M+Na).

Provenance & Evidence