Reaktion #45771

Reaktionsgleichung

hydrochloric acid

trimethylaluminium

N-methylglycine tert-butyl ester hydrochloride

ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

→

compound

Ausbeute 87.3%

tert-Butyl [(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carbonyl)methylamino]acetate

Ausbeute 87.3%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring for 23 hours
2. 2
   workup.ADDITIONwas added to the reaction liquid
3. 3
   Temperaturwith cooling with ice
4. 4
   workup.STIRRINGby stirring at room temperature
5. 5
   Sonstigethe reaction liquid
6. 6
   Extraktionwas extracted with chloroform
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenthe filtrate was concentrated under reduced pressure
10. 10
    Waschenwashed in diethyl ether

Vorschrift

Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution, 4.50 ml, 4.63 mmol) was dropwise added at room temperature to a dichloromethane (6 ml) solution of N-methylglycine tert-butyl ester hydrochloride (840 mg, 4.63 mmol), followed by stirring for 25 hours. Subsequently, a dichloromethane (4 ml) solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (500 mg, 1.54 mmol) was dropwise added, followed by stirring for 23 hours. After the reaction, aqueous 1 N hydrochloric acid solution was added to the reaction liquid with cooling with ice, followed by stirring at room temperature, and the reaction liquid was extracted with chloroform. Next, the obtained organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was suspended and washed in diethyl ether to obtain the entitled compound (569 mg, 87%) as a white solid.

Quelle