Reacción #810595

Ecuación de reacción

acetyl chloride

triethylamine

(8R,9R)-2-methyl-9-phenyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridin-7-one

acetyl chloride

triethylamine

→

title compound

(8R,9R)-10-Acetyl-2-methyl-9-phenyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridin-7-one

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais warmed up to 25° C.
2. 2
   workup.STIRRINGstirred at this temperature for 1 h
3. 3
   OtroSubsequently the reaction is quenched
4. 4
   workup.ADDITIONby adding of saturated aqueous ammonium chloride solution
5. 5
   ExtracciónThis mixture is extracted twice with dichloromethane
6. 6
   LavadoThe combined organic layers are washed with brine
7. 7
   Secadodried over sodium sulphate
8. 8
   Otroevaporated in vacuo
9. 9
   OtroThe crude product is crystallised from diethyl ether

Procedimiento

To a of 0° C. cooled solution of 7.00 g (18.5 mmol) (8R,9R)-2-methyl-9-phenyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridin-7-one in toluene (70 ml) is added 4.10 ml (55.5 mmol) acetyl chloride and 7.70 ml (55.5 mmol) triethylamine and the reaction mixture is stirred for 1 h at 0° C. Afterwards further 4.10 ml (55.5 mmol) acetyl chloride and 7.70 ml (55.5 mmol) triethylamine are added to the reaction mixture and it is warmed up to 25° C. and stirred at this temperature for 1 h. Subsequently the reaction is quenched by adding of saturated aqueous ammonium chloride solution. This mixture is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is crystallised from diethyl ether to provide 5.4 g (12.7 mmol/70%) of the title compound as a colourless solid with a melting point of 168–169° C. (diethyl ether).

Fuente