1-Hydroxybenzotriazole → Oritavancin

Participants

Reaction Steps

Oritavancin diphosphate 5 (630.7 mg, 0.3171 mmol), HBTU (601.1 mg, 1.585 mmol) and HOBt (173.4 mg, 1.283 mmol) was dissolved in the mixture of DMSO (4 mL) and DMF (8 mL) and 0.4 mL (2.296 mmol) of DIPEA was added. After stirring at room temperature for 30 min, the solution of 102 in 1 mL DMF was added plus 1 mL rinse. A yellow clear solution was obtained. After 2 days, 250 mL of diethyl ether was added to the reaction while stirring. After stand for a few min, the clear solution was decanted. The process was repeated with another 150 mL of diethyl ether. The residual mixture was dried in vacuo. The product was purified on repetitive C18 flash columns on a Biotage automatic chromatography system with gradient elution of H3PO4 (30 mM)-triethylamine (20 mM) buffer (aq, pH3)/methanol and then C18 column on Biotage system with gradient elution of 0.1% formic acid buffer (aq, pH2)/methanol. The purified product is a white solid as penta-formate salt (43.2 mg, 6%): ESI-MS calculated for C93H111Cl3N12O27: calculated 484.8 (M/4+H), 646.1 (M/3+H), 967.6 (M/2+H). found: 484.6, 646.0, 967.6.

Provenance & Evidence