Sodium Bicarbonate → Oritavancin

Participants

Reaction Steps

To oritavancin bisphosphoric acid salt (5, 1.0 g, 0.50 mmol) in 1,4-dioxane (15 mL) and H2O (15 mL) was added NaHCO3 (92.91 mg, 1.10 mmol) and the mixture was stirred until all of 5 had dissolved. A solution of 18 (311 mg, 0.60 mmol) in 1,4-dioxane (4 mL) was added and the resulting solution was stirred at room temperature for 20 h. The dioxane was evaporated and the product was precipitated by addition of acetone:diethyl ether (1:3, 100 mL), filtered and dried. The crude product was purified by C18 reversed phase chromatography on a Biotage™ flash chromatography system (10% to 70% MeCN in 0.05% aqueous TFA) to give 19 (720 mg, 65%) as a white solid: ESI-MS calculated for C104H124C13N11O35, 2194.5. found 2195.6 (M+H).

Provenance & Evidence