Reacción #1625

Ecuación de reacción

Potassium carbonate

(R)-2-(4-hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester

Methyl bromoacetate

→

title compound

(R)-4-(2-t-Butoxycarbonylaminopropyl)phenoxyacetic acid, methyl ester

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was heated
2. 2
   Temperaturaat reflux for 3 hours
3. 3
   OtroThe solvent was removed under reduced pressure
4. 4
   Lavadowashed with water (2×30 ml)
5. 5
   SecadoThe organic extracts were dried with sodium sulfate
6. 6
   Otrothe solvent evaporated in vacuo
7. 7
   OtroThe crude product was purified by chromatography on Kieselgel 60 (eluting with 20% ethyl acetate in pentane)

Procedimiento

Potassium carbonate (1.95 g, 14.2 mMol) was added to a solution of (R)-2-(4-hydroxyphenyl)-1-methylethylcarbamic acid, t-butyl ester (2.96 g, 11.8 mMol) in acetone (50 ml) at room temperature under argon. Methyl bromoacetate (1.81 g, 11.8 mMol) was added dropwise and the reaction mixture was heated at reflux for 3 hours. The solvent was removed under reduced pressure and the residue was taken into ethyl acetate and washed with water (2×30 ml). The organic extracts were dried with sodium sulfate and the solvent evaporated in vacuo. The crude product was purified by chromatography on Kieselgel 60 (eluting with 20% ethyl acetate in pentane) to give the title compound as an oil.

Fuente