Ammonia → HCID 86695215, compound

Participants

Reaction Steps

Ammonia gas was introduced in 50 mL of CH3OH at 5° C. for 15 min. To the above solution was added tert-butyl N-methyl-N-(4-[[(3R)-3-(2-oxoethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)carbamate (700 mg, 1.57 mmol, 1.00 equiv), NaCN (93.1 mg, 1.90 mmol, 1.20 equiv) and NH4Cl (92.5 mg, 1.73 mmol, 1.10 equiv) successively. The resulting mixture was stirred for 16 h at room temperature and concentrated under reduced pressure. The residue was applied onto a silica gel column with dichloromethane/methanol (1:30) to afford tert-butyl N-(4-[[(3R)-3-(2-amino-2-cyanoethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (600 mg, 81%) as a yellow oil.

Provenance & Evidence