Reaktion #214751

Reaktionsgleichung

triethylamine

L-alanine ethyl ester hydrochloride

3-(chloromethyl)-2-nitrotoluene

→

N-(3-methyl-2-nitrobenzyl)-L-alanine ethyl ester

Lösungsmittel

ethanol

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigea clear solution resulting
2. 2
   TemperaturThereafter, the temperature was increased to 80° C.
3. 3
   SonstigeThereafter, the mixture was evaporated to dryness under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in 600 ml of water
5. 5
   ExtraktionThe solution was extracted three times with methylene chloride
6. 6
   Waschenthe extracts were washed successively with water and with saturated sodium chloride solution
7. 7
   Sonstigedried
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe thus-obtained crude product
10. 10
    Sonstigewas purified by chromatography on silica gel
11. 11
    Waschenfor the elution

Vorschrift

A solution of 120 ml of triethylamine in 200 ml of absolute ethanol was added dropwise over a period of 30 minutes to a solution of 91.8 g of L-alanine ethyl ester hydrochloride in 300 ml of absolute ethanol. The mixture was warmed to 60° C., a clear solution resulting. To this solution was added dropwise within 1 hour a solution of 55.5 g of 3-(chloromethyl)-2-nitrotoluene in 300 ml of absolute ethanol. Thereafter, the temperature was increased to 80° C. and the mixture was stirred at this temperature overnight. Thereafter, the mixture was evaporated to dryness under reduced pressure and the residue was dissolved in 600 ml of water. The solution was extracted three times with methylene chloride and the extracts were washed successively with water and with saturated sodium chloride solution, dried and evaporated. The thus-obtained crude product was purified by chromatography on silica gel using methylene chloride/5% methanol for the elution. There was obtained N-(3-methyl-2-nitrobenzyl)-L-alanine ethyl ester in the form of a yellow oil; [α]D =-36° (c=1% in methanol).

Quelle