Sodium Cyanide → HCID 86695203, compound

Participants

Reaction Conditions

Reaction Steps

To a 50-mL round-bottom flask containing a solution of tert-butyl N-(4-[[(3S)-3-[(methanesulfonyloxy)methyl]-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 (1.0 g, 1.95 mmol, 1.00 equiv) in DMSO (12 mL) was added NaCN (479 mg, 9.78 mmol, 5.00 equiv) and 4-dimethylaminopyridine (30 mg, 0.25 mmol, 0.13 equiv) and the solution was stirred for 2.5 h at 80° C. After cooling, the reaction was then quenched by the addition of water, extracted with 3×100 mL of ethyl acetate. The organic layers were combined, 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 the desired 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 (830 mg, 96%) as a white solid.

Provenance & Evidence