1,1'-Carbonyldiimidazole → HCID 24801847, compound

Participants

Reaction Steps

A mixture of (2R,6S,13aS,14aR,16aS,Z)-2-(biphenyl-4-yl)-6-(tert-butoxycarbonylamino)-2-methoxy-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylic acid (50 mg, 0.079 mmol) and CDI (755 mg, 4.66 mmol) in tetrahydrofuran (5 mL) was heated at reflux for 1 h. It was then cooled to rt, and then cyclopropanesulfonamide (11.51 mg, 0.095 mmol) was added, followed by DBU (0.042 mL, 0.277 mmol). This reaction mixture was stirred at rt for 18 h, and then concentrated in vacuo to give the crude product as a light colored oil. Purification by preparative HPLC gave 15 mg (26%) of tert-butyl (2R,6S,13aS,14aR,16aS,Z)-2-(biphenyl-4-yl)-14a-(cyclopropylsulfonylcarbamoyl)-2-methoxy-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-ylcarbamate as a white solid.

Provenance & Evidence