Reacción #45905

Ecuación de reacción

tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate

→

solid

Rendimiento 59.6%

4-Cyano-N,N,5-trimethyl-7-[3-(methylamino)cyclopent-2-enyl]-6-phenyl-1,3-benzoxazole-2-carboxamide

Rendimiento 59.6%

Disolventes

hydrochloric acid 1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated away under reduced pressure
2. 2
   workup.ADDITIONethanol was added to the resulting residue
3. 3
   Concentraciónfollowed by concentration under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in chloroform (15 ml)
5. 5
   workup.STIRRINGan aqueous saturated sodium hydrogencarbonate solution (15 ml), and vigorously stirred for 10 minutes
6. 6
   OtroThe aqueous layer was separated
7. 7
   Extracciónextracted twice with chloroform
8. 8
   Lavadowashed with saturated brine
9. 9
   Secadodried over anhydrous sodium sulfate
10. 10
    OtroThe insoluble matter was separated by filtration
11. 11
    Otrothe solvent was evaporated away
12. 12
    Otrothe resulting residue was purified by preparative TLC (eluent, chloroform
13. 13
    Otromethanol=9:1, v/v), and this was further purified by preparative TLC (eluent, chloroform
14. 14
    workup.ADDITION7 N ammonia-containing methanol solution=93:7

Procedimiento

tert-Butyl {3-[4-cyano-2-dimethylcarbamoyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl]cyclopent-2-enyl}methylcarbamate (I-340-2) (154 mg, 0.31 mmol) was dissolved in 4 N hydrochloric acid/1,4-dioxane solution (3 ml), and stirred at room temperature for 1 hour. The solvent was evaporated away under reduced pressure, then ethanol was added to the resulting residue, followed by concentration under reduced pressure. This operation was repeated once again. The residue was dissolved in chloroform (15 ml) and an aqueous saturated sodium hydrogencarbonate solution (15 ml), and vigorously stirred for 10 minutes. The aqueous layer was separated, extracted twice with chloroform. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1, v/v), and this was further purified by preparative TLC (eluent, chloroform:7 N ammonia-containing methanol solution=93:7, v/v) to obtain a brown solid (74 mg). The solid was washed in slurry with diisopropyl ether, and a pale brown solid was collected by filtration. The solid was dried at 60° C. under reduced pressure for 48 hours to obtain the entitled compound (57 mg, 46%).

Fuente