HCID 178502328, compound → HCID 178502322, compound

Participants

Reaction Steps

To (2S,4S)-tert-butyl 2-(1-amino-6-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-naphtho[1,2-d]imidazol-7-yl) naphthalen-2-ylcarbamoyl)-4-(methylthio)pyrrolidine-1-carboxylate (95 mg, 0.12 mmol) in acetic acid (4 mL) and the reaction mixture stirred for 16 hours. Concentrated in vacuo and diluted with EtOAc, washed with sat. NaHCO3 aqueous (2×) and sat. NaCl aqueous (1×). The organic layer was concentrated down after drying over sodium sulfate and subject to silica gel chromatography with an eluent of ethyl acetate and hexane at a gradient of 40-100% with an ISCO column (12 g silica gel). The fractions containing product were combined and the solvent was removed under reduced pressure to provide tert-butyl (2S,4S)-2-(2′-{(2S)-1-[N-(methoxycarbonyl)-L-valyl]pyrrolidin-2-yl}-1H,1′H-7,7′-binaphtho[1,2-d]imidazol-2-yl)-4-(methylsulfanyl)pyrrolidine-1-carboxylate (50 mg, 54%). MS (ESI) m/z 777 [M+H]+.

Provenance & Evidence