تفاعل #355762

معادلة التفاعل

azithromycin

NaHCO3

5-bromovaleric acid

triethylamine

pivaloyl chloride

→

pure product

المردود 108.6%

Cladinose

المردود 108.6%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred for three days at room temperature
2. 2
   أخرىthe layers were separated
3. 3
   استخلاصThe aqueous layer was twice more extracted with 40 ml of CH2Cl2
4. 4
   غسيلThe combined organic extracts were washed with a saturated NaCl solution
5. 5
   تجفيفdried over K2CO3
6. 6
   أخرىevaporated in a rotary evaporator
7. 7
   أخرىThe obtained oily product was purified on a silica gel column (eluant: CH2Cl2:CH3OH:NH4OH=90:9:1.5)

الإجراء التجريبي

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+)

المصدر