반응 #214751

반응 방정식

triethylamine

L-alanine ethyl ester hydrochloride

3-(chloromethyl)-2-nitrotoluene

→

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

용매

ethanol

ethanol

ethanol

반응 조건

후처리

1. 1
   기타a clear solution resulting
2. 2
   온도Thereafter, the temperature was increased to 80° C.
3. 3
   기타Thereafter, the mixture was evaporated to dryness under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in 600 ml of water
5. 5
   추출The solution was extracted three times with methylene chloride
6. 6
   세척the extracts were washed successively with water and with saturated sodium chloride solution
7. 7
   기타dried
8. 8
   기타evaporated
9. 9
   기타The thus-obtained crude product
10. 10
    기타was purified by chromatography on silica gel
11. 11
    세척for the elution

실험 절차

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).

출처