반응 #342763

반응 방정식

L-glutamic acid

L-phenylalanine benzyl ester toluenesulfonic acid

N-ethylmorpholine

dicyclohexylcarbodiimide

→

L-glutamyl-L-phenylalanine benzyl ester

용매

dimethylformamide

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred in an ice water bath for 1 hour
2. 2
   기타at room temperature
3. 3
   기타overnight
4. 4
   기타Dicyclohexylurea was removed by filtration
5. 5
   세척the product was washed in ethyl acetate
6. 6
   기타Solvents of the combined filtrates were removed under reduced pressure with a rotary evaporator at 40° C
7. 7
   workup.ADDITIONEthyl acetate (25 ml) was added to the residue
8. 8
   세척the organic solution was washed until neutral
9. 9
   건조The organic phase was dried over anhydrous MgSO4
10. 10
    여과filtered
11. 11
    기타the solvent was removed with a rotary evaporator
12. 12
    기타The material was crystalized from isopropanol and ether, yield: 1.01 g of white needles, m.p. 103°-104.5° C

실험 절차

A solution of 0.52 g of pyro-L-glutamic acid, 1.72 g of L-phenylalanine benzyl ester toluenesulfonic acid and 0.55 mg of N-ethylmorpholine in 5 ml of dimethylformamide (DMF) and 20 ml of dichloromethane was cooled in an ice bath with stirring. A solution of 0.826 g of dicyclohexylcarbodiimide in 2 ml dichloromethane was added to the above reaction mixture. The reaction mixture was stirred in an ice water bath for 1 hour and then at room temperature overnight. Dicyclohexylurea was removed by filtration and the product was washed in ethyl acetate. Solvents of the combined filtrates were removed under reduced pressure with a rotary evaporator at 40° C. Ethyl acetate (25 ml) was added to the residue and the organic solution was washed until neutral. The organic phase was dried over anhydrous MgSO4, filtered and then the solvent was removed with a rotary evaporator. The material was crystalized from isopropanol and ether, yield: 1.01 g of white needles, m.p. 103°-104.5° C. The material was homogeneous on all TLC and electrophoresis systems.

출처