Cesium carbonate → Methyl (2S,4R)-4-[(6-bromo-7-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)oxy]-1-[(2S)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylacetyl]pyrrolidine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a 0.27 M solution of hydroxyl-quinolinone from Step 3 (1 eq.) and brosylate from Step 2 (1 eq.) in N-methyl-2-pyrrolidinone was added cesium carbonate (1.5 eq.) and the resulting mixture was heated at 60° C. for 16 h. The mixture was cooled to RT and partitioned between water and EtOAc. The organic phase was washed with brine, dried (Na2SO4) and the volatiles were removed under reduced pressure. The residue was purified by SiO2 gel chromatography (eluting with 50% EtOAc/Hex and then 0-5% MeOH/DCM) to yield the title compound. MS (ES+) C29H38BrN3O8 requires: 637. Found: 636, 638 (M+H+).

Provenance & Evidence