Water → Oritavancin

Participants

Reaction Steps

A suspension of 5 (538 mg, 0.270 mmol) and NaHCO3 (68 mg, 0.81 mmol) in dioxane/water (1:1, 12 mL) was stirred at room temperature for approximately 15 min, after which all 5 had dissolved. A solution of 68 (295 mg, 0.541 mmol) in 2 mL dioxane was then added and the resulting solution was stirred at room temperature for 18 h. Cold water was added and the resulting mixture was stirred for 1 h then the precipitate was collected by filtration to give 69 (620 mg, 103%). The crude material which likely contained NaHCO3 was found to be a mixture of the desired product and the monodeprotected material that was used without purification: ESI-MS (M+2H) calculated for C104H130Cl3N10O32PSi2, 1112.4. found 1112.5.

Provenance & Evidence