Reaktion #1057270

Reaktionsgleichung

(S)-tyrosine methyl ester

4-(bromoacetyl)benzonitrile

sodium thiocyanate

→

Methyl (2S)-2-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-3-(4-hydroxyphenyl)propionate

Ausbeute 53.0%

Lösungsmittel

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter removing ethanol
2. 2
   workup.DISTILLATIONby distillation, water and ethyl acetate
3. 3
   workup.ADDITIONwere added
4. 4
   ExtraktionAqueous phase was extracted twice with ethyl acetate
5. 5
   Trocknenwere dried over sodium sulfate
6. 6
   Sonstigethe solvent was evaporated
7. 7
   SonstigeThe product was purified by chromatography (SiO2, ethyl acetate/hexane)

Vorschrift

22.3 g (0.1 mol) of 4-(bromoacetyl)benzonitrile and 8.66 g (0.107 mol) of dry sodium thiocyanate in ethanol (200 ml) were stirred for 3 h at 50° C. Then 19.51 g (0.1 mol) of (S)-tyrosine methyl ester in ethanol (100 ml) was added in one portion and the reaction mixture was stirred for 12 h. After removing ethanol by distillation, water and ethyl acetate were added. Aqueous phase was extracted twice with ethyl acetate, combined organic phases were dried over sodium sulfate and the solvent was evaporated. The product was purified by chromatography (SiO2, ethyl acetate/hexane). The yield was 53%. MS (ES) 379 (M+, 100%)

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