반응 #51335

반응 방정식

N-(3,5-dimethoxyphenyl)alanine

3,5-dimethoxyaniline

2-chloropropionic acid

chlorotrimethylsilane

→

title compound

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

용매

iso-butanol

반응 조건

후처리

1. 1
   온도the reaction mixture refluxed overnight
2. 2
   기타The excess alcohol was removed at reduced pressure
3. 3
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate
4. 4
   세척The ethyl acetate solution was washed with saturated aqueous NaHCO3
5. 5
   건조dried with Na2SO4
6. 6
   기타the solvent removed

실험 절차

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.

출처