1,1'-Carbonyldiimidazole → HCID 16734903, compound

Participants

Reaction Steps

To a solution of DC101SMe ((S)—N-(2-(1-(chloromethyl)-5-hydroxy-2,3-dihydro-1H-benzo[e]indole-3-carbonyl)-1H-indol-5-yl)-3-(methyldisulfanyl)propanamide, 100 mg 0.19 mmol) in 10 ml of DMA was added DIPEA (35 μl, 0.20 mmol). After stirred under Ar for 3 min., 32.0 mg (0.20 mmol) of carbonyldiimidazole was added. The mixture was stirred for 2 hours and TLC showed all DC101SMe was consumed, then fresh prepared 3-aminobenzenesulfonate diisopropylethylamine salt (65 mg, 0.21 mmol) was added. The mixture was stirred under Ar for 24 h and HPLC showed the reaction completed to form DC107SMe [(S)-3-((1-(chloromethyl)-3-(5-(3-(methyldisulfanyl)propanamido)-1H-indole-2-carbonyl)-2,3-dihydro-1H-benzo[e]indol-5-yloxy)carbonylamino)benzenesulfonic acid]. The mixture was concentrated to ˜5 ml with oil pump and used directly for next step without further purification.

Provenance & Evidence