Reaktion #1625

Reaktionsgleichung

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

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle