Potassium Carbonate → (S)-tert-butyl (4-methyl-1-((6-methyl-9-(oxazol-5-yl)-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-tert-butyl (1-((9-formyl-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (100 mg, 0.220 mmol), K2CO3 (33.5 mg, 0.243 mmol) and TOSMIC (47.4 mg, 0.243 mmol) in MeOH (5 mL) was heated at 60° C. for 2 h. After cooling, the MeOH was removed under reduced pressure and residue was taken up in ethyl acetate. The organic layer was washed with H2O, followed by saturated NaHCO3, dried over Na2SO4 and concentrated under reduced pressure to afford (S)-tert-butyl (4-methyl-1-((6-methyl-9-(oxazol-5-yl)-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate (50 mg, 0.054 mmol, 24% crude yield) as a gum. The material was carried on without further purification. LC/MS (ESI) m/e 493.4, [(M+H)+, calcd for C27H33N4O5, 493.6]; LC/MS retention time (method E): tR=1.08 min.

Provenance & Evidence