Reaktion #62908

Reaktionsgleichung

pyroglutamic acid

n-decanol

dicyclohexylcarbodiimide

→

Decyl Pyroglutamate

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Sonstigethe cooling bath was removed
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature overnight
4. 4
   SonstigeThe dichloromethane was evaporated off
5. 5
   Filtrationfiltered
6. 6
   WaschenThe filtrate was washed with 1N HCl, water, aqueous bicarbonate and water
7. 7
   TrocknenIt was then dried over Na2SO4
8. 8
   Sonstigeevaporated
9. 9
   SonstigeIt was chromatographed over silica gel
10. 10
    WaschenThe pure decyl ester was eluted with ethylacetate-chloroform (1:4), 2.3 g m.p. 34°-35°

Vorschrift

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 HCl, 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°.

Quelle