Réaction #1625

Équation de réaction

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

Solvants

acetone

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source