Methyl iodide → HCID 86695207, compound

Participants

Reaction Steps

To a 50-mL round-bottom flask containing a solution of tert-butyl N-(4-[[(3R)-3-(cyanomethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]-1-methylcyclohexyl)carbamate (100 mg, 0.23 mmol, 1.00 equiv) in distilled DMF (3 mL) was added sodium hydride (60% dispersion in mineral oil 37 mg, 0.93 mmol, 4.09 equiv) at 0° C. The resulting solution was stirred for 0.5 h at this temperature. Then CH3I (321 mg, 2.26 mmol, 1.00 equiv) was added and the resulting solution was allowed to react, with stirring, for an additional 2 h at 30° C. The reaction was then quenched with saturated aqueous NH4Cl and extracted with 3×30 mL of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:2) to give tert-butyl N-(4-[[(3R)-3-(cyanomethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]-1-methylcyclohexyl)-N-methylcarbamate (80 mg, 78%) as a white solid.

Provenance & Evidence