반응 #345429

반응 방정식

dicyclohexylcarbodiimide

3-formyl-4-hydroxybenzoic acid

N-hydroxysuccinimide

phenylalanine methyl ester hydrochloride

triethylamine

→

N-(3-Formyl-4-hydroxybenzoyl)phenylalanine methyl ester

용매

chloroform

dimethylformamide

반응 조건

후처리

1. 1
   기타After re-equilibrating to room temperature
2. 2
   여과The precipitate is then filtered
3. 3
   온도The filtrate is cooled to 8° C.
4. 4
   workup.ADDITIONtreated dropwise
5. 5
   workup.STIRRINGwith stirring, with a suspension
6. 6
   workup.STIRRINGThe mixture is stirred for 3 hours at 20° C.
7. 7
   workup.WAITfor 5 hours at 50° C
8. 8
   온도After cooling
9. 9
   기타evaporation of the solvents
10. 10
    세척After washing this solution with 1N hydrochloric acid
11. 11
    건조with water, the organic phase is dried
12. 12
    기타evaporated
13. 13
    기타The oily residue leads to the expected product by crystallization from toluene

실험 절차

87 mmol of dicyclohexylcarbodiimide are added to a stirred suspension, cooled to 10° C, containing 80 mmol of 3-formyl-4-hydroxybenzoic acid (prepared according to H. WYMBERG, J. Am. Chem. Soc., 76, 4998, 1954) and 87 mmol of N-hydroxysuccinimide in 320 ml of chloroform. After re-equilibrating to room temperature, the mixture is kept stirring overnight. The precipitate is then filtered. The filtrate is cooled to 8° C. and treated dropwise, with stirring, with a suspension containing 160 mmol of phenylalanine methyl ester hydrochloride and 160 mmol of triethylamine in 100 ml of anhydrous dimethylformamide. The mixture is stirred for 3 hours at 20° C. and then for 5 hours at 50° C. After cooling and evaporation of the solvents, the residue is taken up in 400 ml of ethyl acetate. After washing this solution with 1N hydrochloric acid and then with water, the organic phase is dried and evaporated. The oily residue leads to the expected product by crystallization from toluene.

출처