Triethylamine → 3-O-Methylmycarose

Participants

Reaction Steps

To a solution of 5-bromovaleric acid (1.282 g; 7.07 mmole) in dry CH2Cl2 (10 ml), 1 ml (7.23 mmole) of triethylamine, 868 mg (7.10 mmole) of 4-dimethyl-aminopyridine and 0.940 ml (7.63 mmole) of pivaloyl chloride were added. The solution was stirred for 2 hours at room temperature in a flow of argon and then a solution of azithromycin (2 g; 2.67 mmole) in 10 ml of dry CH2Cl2 was added. The reaction mixture was stirred for three days at room temperature. Subsequently, 60 ml of saturated NaHCO3 solution were added to the reaction mixture and the layers were separated. The aqueous layer was twice more extracted with 40 ml of CH2Cl2. The combined organic extracts were washed with a saturated NaCl solution, dried over K2CO3 and evaporated in a rotary evaporator. The obtained oily product was purified on a silica gel column (eluant: CH2Cl2:CH3OH:NH4OH=90:9:1.5). 511 mg of the pure product were obtained. MS(ES+): 912 (MH+)

Provenance & Evidence