Sodium Bicarbonate → Oritavancin

Participants

Reaction Steps

To oritavancin bisphosphoric acid salt (5, 223 mg, 0.112 mmol) in 1,4-dioxane (5 mL) and H2O (6 mL) was added NaHCO3 (29 mg, 0.35 mmol) and the mixture was stirred until all of 5 had dissolved. A solution of 31 (125 mg, 0.165 mmol) in 1,4-dioxane (2 mL) was added and the resulting solution was stirred at room temperature overnight. The product was precipitated by the addition of H2O and collected by filtration. The crude product was purified by C18 reversed phase chromatography on a Biotage™ flash chromatography system (30% to 80% MeCN in 0.2% TEA/phosphate pH 3) to give 35 (110 mg, 37%, based on the di-phosphoric acid salt) as a white solid: ESI-MS (M+2H) calculated for C118H155Cl3N14O35, 1218.9. found 1218.4.

Provenance & Evidence