Dichloromethane → HCID 67434511, compound

Participants

Reaction Conditions

Reaction Steps

A Heterogeneous mixture of (S)-(9H-fluoren-9-yl)methyl 1-(4-fluoro-2-(4-fluorophenylamino)phenylamino)-1-oxopropan-2-ylcarbamate (3.500 g, 6.82 mmol) in acetic acid (45.4 mL) was heated at 100° C. with stirring. After 26 h, the mixture was cooled to rt and poured into DCM (100 mL) and satd. aq. NaHCO3 solution (100 mL). The aq. layer was removed and the organic layer was washed with satd. aq. NaHCO3 solution (100 mL×1), water (100 mL×1) and brine (100 mL×1), dried over MgSO4, filtered, and concentrated under reduced pressure to give (S)-(9H-fluoren-9-yl)methyl 1-(6-fluoro-1-(4-fluorophenyl)-1H-benzo[d]imidazol-2-yl)ethylcarbamate as a dark brown syrup: LC-MS (ESI) m/z 496.1 [M+H]+. Epimerization occurred during cyclization and the dark brown syrup was carried on crude without further purification.

Provenance & Evidence