Hydrogen Peroxide → HCID 86695217, compound

Participants

Reaction Conditions

Reaction Steps

To a 50-mL round-bottom flask containing a solution of benzyl N-[2-[(3R)-12-[(4-[[(tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-3-yl]-1-cyano ethyl]carbamate (450 mg, 0.74 mmol, 1.00 equiv) in methanol (20 mL) was added LiOH.H2O (94 mg, 2.24 mmol, 3.00 equiv) and H2O2 (30%, 2 mL) at 0° C. The resulting solution was stirred for 2 h at 0° C. and quenched with saturated aqueous Na2SO3 and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5-1:3) to afford the corresponding benzyl N-[(1S)-2-[(3R)-12-[(4-[[(tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-3-yl]-1-carbamoylethyl]carbamate (167.3, 230 mg) as a white solid and benzyl N-[(1R)-2-[(3R)-12-[(4-[[(tert-butoxy)carbonyl](methyl)amino]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2 (6),9,11-tetraen-3-yl]-1-carbamoylethyl]carbamate (167.4, 90 mg) as a white solid.

Provenance & Evidence