Triethylamine → HCID 86695202, compound

Participants

Reaction Steps

To a solution of tert-butyl N-(4-[[(3S)-3-(hydroxymethyl)-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, 2.31 mmol, 1.00 equiv) in dichloromethane (20 mL) was added MsCl (632 mg, 5.54 mmol, 2.40 equiv) and triethylamine (839 mg, 8.29 mmol, 3.59 equiv) at 0° C. The resulting solution was stirred for 1 h at room temperature and quenched with water. The resulting solution was extracted with 3×50 mL of DCM and the organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/3) to yield 1.07 g (91%) 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 as a light yellow oil.

Provenance & Evidence