HCID 178502181, compound → HCID 178502418, compound

Participants

Reaction Steps

To (1-{2-[5-(6-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-4,5-dihydro-1H-naphtho[1,2-d]imidazol-7-yl}-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (13.0 mg, 0.016 mmol) in CH2Cl2 (1 mL) was added MnO2 (2.8 mg, 0.032 mmol). The reaction was stirred overnight then additional MnO2 (1.4 mg, 0.016 mmol) was added. After stirring for 3 hours, the reaction was filtered through a Whatman 0.45 mM PTFE filter. The filtrate was concentrated then purified by preparative reverse phase HPLC (Gemini, 10 to 45% ACN/H2O+0.1% TFA) to yield methyl (S)-1-((S)-2-(5-(6-(2-((S)-1-((S)-2-methoxycarbonylamino-3-methylbutanoyl)pyrrolidin-2-yl)-1H-naphtho[1,2-d]imidazol-7-yl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (6.3 mg, 48%). LCMS-ESI+: calculated for C46H53N8O6: 813.4; observed [M+1]+: 813.4.

Provenance & Evidence