Potassium Carbonate → HCID 58459264, compound

Participants

Reaction Steps

Boc-L-Ala-OH (3.00 g, 15.86 mmol) and 3,4-diamino-1-fluorobenzene (2.00 g, 15.86 mmol) were mixed in pyridine (52.9 mL). EDCBCl (9.12 g, 47.6 mmol) was added and the mixture was stirred at ambient temperature for 20 min. The reaction mixture was diluted with EtOAc, washed with water, 1.0 N HCl and brine. The organic layer was dried with Na2SO4, filtered, and concentrated. The crude residue was purified by column chromatography on a 120 g of Redi-Sep™ column using 0 to 100% gradient of EtOAc in hexane as eluent. The desired fractions were combined and concentrated under reduced pressure to give the crude amide intermediate. The amide was dissolved in AcOH (26.9 mL) and heated in an oil bath at 70° C. for about 30 min. The reaction mixture was diluted with EtOAc and carefully neutralized with aq. K2CO3. The organic layer was washed with NaCl, dried with Na2SO4, and filtered. The filtrate was concentrated to dryness to yield (S)-tert-butyl 1-(6-fluoro-1H-benzo[d]imidazol-2-yl)ethylcarbamate: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.23 (1H, br. s.), 7.15-7.61 (3H, m), 6.98 (1H, t, J=8.5 Hz), 4.78-4.89 (1H, m), 1.46 (3H, d, J=7.0 Hz), 1.40 (9H, s); LC-MS (ESI) m/z 280.1 [M+H]+.

Provenance & Evidence