HCID 59722694, compound → HCID 59722712, compound

Participants

Reaction Steps

Ethylmagnesium bromide (3 M in ether; 0.17 mL, 0.51 mmol) was added dropwise over 15 min to a solution of titanium(IV) isopropoxide (0.08 mL, 0.26 mmol) and methyl (6S,9R)-9-[(tert-butoxycarbonyl)amino]-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepine-3-carboxylate (54 mg, 0.13 mmol) in ether (0.9 mL) at 0° C. After 1.5 h, additional titanium(IV) isopropoxide (0.08 mL, 0.26 mmol) and ethylmagnesium bromide (3 M in ether; 0.17 mL, 0.51 mmol) were added. After 1.5 h, the mixture was quenched with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic layers were washed with saturated brine, dried with magnesium sulfate, filtered, and concentrated. Purification by reverse phase HPLC (C-18, 80% water/acetonitrile→40% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (23 mg). MS 420.2 (M+1).

Provenance & Evidence