Ethanol → HCID 90067288, compound

Participants

Reaction Steps

TFA (3.2 ml, 41.5 mmol) was added to a stirred solution of tert-butyl 2-[4-[2-[[(3R,3aR,6R,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-yl]oxy]-1-allyl-6-chloro-imidazo[4,5-b]pyridin-5-yl]phenyl]-4,6-dihydropyrrolo[3,4-c]pyrazole-5-carboxylate (477.4 mg, 0.649 mmol) in DCM (3.2 ml). The reaction mixture was a pale yellow solution that was stirred at room temperature for 3 days. The reaction mixture was evaporated under reduced pressure to give a light yellow oil. Flash chromatography of the oil utilizing a 40 g silica RediSep Rf® column and employing a 0-10% (10% NH4OH/MeOH)/DCM gradient followed by 10% (10% NH4OH/MeOH)/DCM afforded the title compound as an off-white solid following lyophilization from ethanol and benzene. LC-MS: calculated for C26H25ClN6O4 520.16 observed m/e: 521.15 (M+H)+ (Rt 1.00/2 min)

Provenance & Evidence