Ethyl orthoformate → HCID 49869931, compound

Participants

Reaction Conditions

Reaction Steps

Triethyl orthoformate (70.0 μL, 0.420 mmol) was added to a mixture of 4a (33.0 mg, 0.094 mmol) and sodium azide (20.0 mg, 0.308 mmol) in acetic acid (1.00 mL), and the resulting mixture was heated to 90° C. After 15 h, the reaction mixture was cooled to rt, quenched with satd. aq. NaHCO3 and extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (gradient elution, 0-15% MeOH/DCM as eluent) to afford the title compound, 5a. m/z (ES) 403 (MH)+; IC50=815 nM

Provenance & Evidence