Reacción #1375838

Ecuación de reacción

N-(4-Methylthiophenyl)alanine ethyl ester

n-butyl iodide

potassium carbonate

→

ester

N-(4-Methylthiophenyl)-N-(n-butyl)alanine ethyl ester

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated
2. 2
   Temperaturaat reflux for 48 h under a nitrogen atmosphere
3. 3
   TemperaturaThe reaction mixture was cooled
4. 4
   Otropartitioned between 300 mL ethyl acetate and 200 mL brine
5. 5
   OtroThe organic layer was separated
6. 6
   Lavadowashed with 100 mL brine
7. 7
   Otrodried over anhyd
8. 8
   Concentraciónsodium sulfate, and concentrated at reduced pressure
9. 9
   workup.ADDITIONThe resulting oil was charged onto a silica gel column
10. 10
    Lavadoeluted with heptane:THF (5:1)

Procedimiento

N-(4-Methylthiophenyl)alanine ethyl ester (10.0 g, 42.0 mmol), n-butyl iodide (7.9 g, 42 mmol) and potassium carbonate were added to 150 mL of acetonitrile and the mixture was heated at reflux for 48 h under a nitrogen atmosphere. The reaction mixture was cooled and then partitioned between 300 mL ethyl acetate and 200 mL brine. The organic layer was separated, washed with 100 mL brine, dried over anhyd. sodium sulfate, and concentrated at reduced pressure. The resulting oil was charged onto a silica gel column and eluted with heptane:THF (5:1). The desired ester was isolated as a yellow oil (3.0 g, 24%).

Fuente