Reacción #51335

Ecuación de reacción

N-(3,5-dimethoxyphenyl)alanine

3,5-dimethoxyaniline

2-chloropropionic acid

chlorotrimethylsilane

→

title compound

N-(3,5-dimethoxyphenyl)alanine iso-butyl ester

Disolventes

iso-butanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture refluxed overnight
2. 2
   OtroThe excess alcohol was removed at reduced pressure
3. 3
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate
4. 4
   LavadoThe ethyl acetate solution was washed with saturated aqueous NaHCO3
5. 5
   Secadodried with Na2SO4
6. 6
   Otrothe solvent removed

Procedimiento

N-(3,5-dimethoxyphenyl)alanine (crude, 454 mg) (prepared according to the procedure described in U.S. Pat. No. 3,598,859 using 3,5-dimethoxyaniline (Aldrich) and 2-chloropropionic acid (Aldrich)) was treated in dry iso-butanol (10 mL) with 0.1 mL of chlorotrimethylsilane and the reaction mixture refluxed overnight. The excess alcohol was removed at reduced pressure and the residue dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated aqueous NaHCO3, dried with Na2SO4 and the solvent removed to provide the title compound. The reaction was monitored by silica gel tlc (Rf=0.3 in 20% EtOAc/hexanes). Purification was by preparative thin layer chromatography using 20% EtOAc/hexanes as the eluant.

Fuente