Imidazole → HCID 131735330, compound

Participants

Reaction Conditions

Reaction Steps

A solution of imidazole (64.5 mg, 0.948 mmol) and triphenylphosphine (99 mg, 0.379 mmol) in 1.5 ml DCM was cooled to 0° C. and iodine (96 mg, 0.379 mmol) was added. The mixture was stirred for 2 min at 0° C., then solution of (R)-tert-butyl-N-(5-(2-(3-hydroxypropyl)-5-nitrophenyl)-2,2,5-trimethyl-1,1-dioxido-5,6-dihydro-2H-1,4-thiazin-3-yl)-N-tert-butoxycarbonyl-carbamate (180 mg, 0.316 mmol) in 0.5 ml DCM was added. The mixture was removed from cooling bath and stirred at rt for 20 min. The mixture was directly loaded onto 12 g RediSep Gold column and eluted with 5-50% EtOAc in heptane to afford (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)carbamate-N-tert-butoxycarbonyl-carbamate (173 mg, 0.255 mmol, 81% yield). LC/MS (ESI+) m/z=524 (M Boc−t-Bu).

Provenance & Evidence