Reacción #318654

Ecuación de reacción

pyroglutamic acid

n-decanol

dicyclohexylcarbodiimide

→

Decyl Pyroglutamate

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   Otrothe cooling bath was removed
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature overnight
4. 4
   OtroThe dichloromethane was evaporated off
5. 5
   Filtraciónfiltered
6. 6
   LavadoThe filtrate was washed with 1N HC1, water, aqueous bicarbonate and water
7. 7
   SecadoIt was then dried over Na2SO4
8. 8
   Otroevaporated
9. 9
   OtroIt was chromatographed over silica gel
10. 10
    LavadoThe pure decyl ester was eluted with ethylacetate-chloroform (1:4), 2.3 g m.p. 34-35%

Procedimiento

To an ice cold suspension of pyroglutamic acid (1.3 g) and n-decanol (1.6 g) in dichloromethane (50 ml), dicyclohexylcarbodiimide (2.1 g) and 4-dimethylaminopyridine (0.1 g) were added. After stirring at ice bath temperature for 2 hours, the cooling bath was removed and the mixture was stirred at room temperature overnight. The dichloromethane was evaporated off. The residue was taken in ether and filtered. The filtrate was washed with 1N HC1, water, aqueous bicarbonate and water. It was then dried over Na2SO4 and evaporated. The residue weighed 2.75 g. It was chromatographed over silica gel. The pure decyl ester was eluted with ethylacetate-chloroform (1:4), 2.3 g m.p. 34-35%.

Fuente