tert-Butyl methyl [(3R,4S,5S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-7-vinylquinolin-2-yl)carbonyl]amino}pyridin-4-yl)-5-methylpiperidine-3, 4-diyl]biscarbamate → Methyl [(3R,4S,5S)-3-amino-1-(3-{[(3-amino-7-ethylquinolin-2-yl)carbonyl]amino}pyridin-4-yl)-5-methylpiperidin-4-yl]carbamate

Participants

Reaction Steps

To a solution of tert-butyl methyl [(3R,4S,5S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-7-vinylquinolin-2-yl)carbonyl]amino}pyridin-4-yl)-5-methylpiperidine-3,4-diyl]biscarbamate (92 mg, 0.13 mmol) in MeOH (4.0 mL), 10% Pd on carbon (21 mg) was added. The reaction mixture was deoxygenated under reduced pressure and hydrogen was introduced via a balloon. The reaction mixture was stirred at room temperature under hydrogen for 1 h. The mixture was then filtered and concentrated under reduced pressure. The resulting residue was dissolved in DCM (2 mL), and TFA (2 mL) was added. The mixture then was stirred at room temperature for 1 h before being concentrated under reduced pressure. The residue was purified by preparative LCMS (pH=10 method; XBridge™ preparative C18 5 μm OBD™ column, 30×10 mm, 60 mL/min., eluting with a gradient of MeCN and water with 0.1% NH4OH) to give the title compound as a yellow powder (45 mg, 73%). LCMS calc. for C25H32N7O3 (M+H)+: m/z=478.3. Found: 478.3.

Provenance & Evidence