Carbamate → HCID 86728131, compound

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Reaction Steps

A mixture of cis and trans isomers, tert-butyl N-tert-butoxycarbonyl-N-[2R,3R)-3-(2-fluoro-5-nitro-phenyl)-2-[(2S)-2-hydroxypropyl]-3,6,6-trimethyl-1,1-dioxo-2H-1,4-thiazin-5-yl]carbamate and tert-butyl N-tert-butoxycarbonyl-N-[(2S,3R)-3-(2-fluoro-5-nitro-phenyl)-2-[(2S)-2-hydroxypropyl]-3,6,6-trimethyl-1,1-dioxo-2H-1,4-thiazin-5-yl]carbamate (1.8 g, 3.06 mmol) and cesium carbonate (4.99 g, 15.32 mmol) were combined in DMSO (15 ml) and stirred at room temperature for 6 h. The solution was diluted with water and the precipitate was collected by filtration, washed with water, and dried under vacuum. The product was purified via silica gel column chromatography (80 g column) using 10-50% ethyl acetate in heptane to afford to afford tert-butyl N-[(4aR,6S,11bR)-3,3,6,11b-tetramethyl-10-nitro-4,4-dioxo-5,6-dihydro-4aH-[1]benzoxepino[4,5-b][1,4]thiazin-2-yl]-N-tert-butoxycarbonyl-carbamate (1.62 g, 2.85 mmol, 93% yield). MS m/z=590 [M+Na].

Provenance & Evidence