Sodium Iodide → HCID 89495927, compound

Participants

Reaction Steps

To a solution of (6R,7R)-4-methoxybenzyl 7-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetamido)-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 5-oxide (10.00 g, 12.56 mmol) in Acetone (100 mL) at rt was added sodium iodide (2.82 g, 18.84 mmol). The mixture was stirred at the same temperature over 2 h. LCMS indicated completion of the reaction. The solid was filtered off, the filtrate was concentrated under vacuum, and the residue was purified by Combiflash automated silica gel chromatography (120 g Gold column), eluting with ethyl acetate/hexanes (0-50%) to afford (6R,7R)-4-methoxybenzyl 7-((Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxy carbonyl)amino)thiazol-4-yl)acetamido)-3-(iodomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 5-oxide (10.86 g, 12.23 mmol, 97% yield) as a yellow solid. LCMS: (M+H)+: 887.9.

Provenance & Evidence