HCID 59843177, compound → HCID 86624648, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 58 (62 mg, 0.153 mmol) in dry DMF (0.3 mL) at 0° C. was added (R)-tert-butyl 1-(6-fluoro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-1-thioxopropan-2-ylcarbamate (57.2 mg, 0.169 mmol; J. Med. Chem.1999, 42, 2046-2052) in two equal portions over 10 minutes and the reaction was stirred at 0° C. for 2 hours and then at room temperature for 16 h. It was then diluted with water (˜15 mL) and extracted into dichloromethane using an “IST phase-separator.” The DCM extracts were combined and concentrated and the crude material purified by silica gel chromatography (Biotage 12M, 20% to 30% to 40% ethyl acetate in hexanes) to give 134 (35 mg, 0.059 mmol, 38.6% yield) as white solid. LRMS(ESI): (calc.) 529.3 (found) 614.3 (MNa)+.

Provenance & Evidence