Cesium carbonate → (3aR,7S,10S,12R,21E,24aS)-7-cyclopentyl-N-{(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethenylcyclopropyl}-5,8-dioxo-19-[2-(2-oxo-1,3-oxazolidin-3-yl)ethoxy]-1,2,3,3a,5,6,7,8,11,12,20,23,24,24a-tetradecahydro-10H-9,12-methanocyclopenta[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-10-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of (3aR,7S,10S,12R,21E,24aS)-7-cyclopentyl-N-{(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethenylcyclopropyl}-19-hydroxy-5,8-dioxo-1,2,3,3a,5,6,7,8,11,12,20,23,24,24a-tetradecahydro-10H-9,12-methanocyclopenta[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-10-carboxamide (Example 17) (40 mg) in DMF (0.75 mL) under nitrogen was added cesium carbonate (495 mg) followed by 2-(2-oxo-1,3-oxazolidin-3-yl)ethyl 4-methylbenzenesulfonate (144 mg). The reaction mixture was stirred at room temperature for 30 minutes and at 50° C. for 3 hours. After cooling back to room temperature, the reaction was quenched with water and extracted with ethyl acetate (3×). The combined organic fractions were dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase HPLC (40%-100% ACN/0.15% TFA-water) afforded the desired product (39 mg) after workup with NaHCO3 and ethyl acetate. HRMS (ES+) m/z 903.3933 (M+H)+.

Provenance & Evidence