تفاعل #721034

معادلة التفاعل

n-hexane

triethylamine

(3R,6S)-[6-(9-fluoro-1-hydroxy-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-2-ylmethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

acetic anhydride

→

acetic acid 2-(2S,5R)-(5-tert-butoxycarbonylamino-tetrahydro-pyran-2-ylmethyl)-9-fluoro-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-1-yl ester

المردود 68.0%

المذيبات

ethyl acetate

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction mixture is quenched with ethanol (1 mL), solvents
2. 2
   أخرىare evaporated
3. 3
   أخرىto give a crude product that
4. 4
   أخرىis purified by column chromatography (silica gel, eluent

الإجراء التجريبي

4-Dimethylaminopyridine (16 mg, 0.13 mmol, 0.5 eq) and triethylamine (112 μL, 0.80 mmol, 3.0 eq) are added at 0° C. to a stirred solution of (3R,6S)-[6-(9-fluoro-1-hydroxy-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-2-ylmethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester (120 mg, 0.27 mmol, 1.0 eq) in dichloromethane (10 mL), followed by acetic anhydride (38 μL, 0.40 mmol, 1.5 eq). After 1 hour stirring at 0° C., the reaction mixture is quenched with ethanol (1 mL), solvents are evaporated to give a crude product that is purified by column chromatography (silica gel, eluent: n-hexane:ethyl acetate, 5:1 to 1:1, v/v) to afford acetic acid 2-(2S,5R)-(5-tert-butoxycarbonylamino-tetrahydro-pyran-2-ylmethyl)-9-fluoro-8-methoxy-1,2-dihydro-furo[2,3-c]quinolin-1-yl ester as a light yellow solid (89 mg, 68% yield).

المصدر