Sodium Bicarbonate → Oritavancin

Participants

Reaction Steps

To oritavancin bisphosphoric acid salt (5, 400 mg, 0.20 mmol) in 1,4-dioxane (10 mL) and H2O (10 mL) was added NaHCO3 (37.16 mg, 0.44 mmol) and the mixture was stirred until all of 5 had dissolved. A solution of 11 (98.94 mg, 0.24 mmol) in 1,4-dioxane (3 mL) was added and the resulting solution was stirred at room temperature for 2 days. The solvents were evaporated to dryness. The crude product was purified by C18 reversed phase chromatography on a Biotage™ flash chromatography system (10% to 60% MeCN in 0.05% aqueous TFA) to give 12 (102 mg, 24%) as a white solid: ESI-MS calculated for C100H114Cl3N11O32, 2088.4. found 2089.3 (M+H).

Provenance & Evidence