تفاعل #720985

معادلة التفاعل

{trans-4-[3-(3-benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-2,3-dihydroxy-propyl]-cyclohexyl}-carbamic acid tert-butyl ester

ethyl acetate

→

{trans-4-[5-(3-benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-2-oxo-[1,3]dioxolan-4-ylmethyl]-cyclohexyl}-carbamic acid tert-butyl ester

المردود 96.0%

المذيبات

toluene

—

petroleum ether

ظروف التفاعل

المعالجة

1. 1
   أخرىsolvent is removed
2. 2
   أخرىthe crude is purified by column chromatography (silica gel, eluent

الإجراء التجريبي

N,N′-Carbonyldiimidazole (2.56 g, 15.83 mmol, 5.0 eq) is added at room temperature to a stirred solution of {trans-4-[3-(3-benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-2,3-dihydroxy-propyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.70 g, 3.16 mmol, 1.0 eq) in toluene (150 mL). After 2 hours stirring at 70° C., solvent is removed and the crude is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 5:1, v/v) to afford {trans-4-[5-(3-benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-2-oxo-[1,3]dioxolan-4-ylmethyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (1.70 g, 96% yield).

المصدر