تفاعل #342763

معادلة التفاعل

L-glutamic acid

L-phenylalanine benzyl ester toluenesulfonic acid

N-ethylmorpholine

dicyclohexylcarbodiimide

→

L-glutamyl-L-phenylalanine benzyl ester

المذيبات

dimethylformamide

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred in an ice water bath for 1 hour
2. 2
   أخرىat room temperature
3. 3
   أخرىovernight
4. 4
   أخرىDicyclohexylurea was removed by filtration
5. 5
   غسيلthe product was washed in ethyl acetate
6. 6
   أخرىSolvents 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
   غسيلthe organic solution was washed until neutral
9. 9
   تجفيفThe organic phase was dried over anhydrous MgSO4
10. 10
    ترشيحfiltered
11. 11
    أخرىthe solvent was removed with a rotary evaporator
12. 12
    أخرىThe material was crystalized from isopropanol and ether, yield: 1.01 g of white needles, m.p. 103°-104.5° C

الإجراء التجريبي

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.

المصدر