반응 #63991

반응 방정식

dicyclohexylcarbodiimide

N-t-butoxycarbonyl-L-alanine

D-alanine benzyl ester p-toluenesulfonic acid salt

triethylamine

→

N-t-butoxycarbonyl-L-alanyl-D-alanine benzyl ester

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   여과were filtered
2. 2
   농축the filtrate concentrated to an oil
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 400 ml
4. 4
   세척of ethyl acetate which was washed with a 1% hydrochloric acid solution
5. 5
   기타The organic phase was separated
6. 6
   건조dried over magnesium sulfate
7. 7
   농축concentrated to an oil
8. 8
   기타The residue was triturated with diethyl ether
9. 9
   여과the resulting solids filtered under nitrogen
10. 10
    기타of the desired product crystallized from the filtrate

실험 절차

To a solution of 23.0 g. (0.121 m) of N-t-butoxycarbonyl-L-alanine, 42.6 g. (0.121 m) of D-alanine benzyl ester p-toluenesulfonic acid salt and 17 ml. (0.121 m) of triethylamine in 400 ml. of cold (0° C.) methylene chloride was added dropwise 25.0 g. (0.121 m) of dicyclohexylcarbodiimide in 100 ml. of methylene chloride. After stirring overnight at room temperature the solids were filtered and the filtrate concentrated to an oil. The residue was dissolved in 400 ml. of ethyl acetate which was washed with a 1% hydrochloric acid solution, a 10% potassium carbonate solution, water and a brine solution. The organic phase was separated, dried over magnesium sulfate and concentrated to an oil. The residue was triturated with diethyl ether and the resulting solids filtered under nitrogen, 16.0 g. An additional 12.7 g. of the desired product crystallized from the filtrate.

출처