L-Pyroglutamic Acid → Decyl 5-oxo-L-prolinate

HRID 34630

Reaktionsgleichung

Reaktionsgleichung von HRID 34630
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:8]

Komponenten

6

Edukt 3

HCID 7405L-Pyroglutamic AcidHCID 81741-DecanolHCID 10868Dicyclohexylcarbodiimide

Produkt 1

HCID 22839298Decyl 5-oxo-L-prolinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  1. additionwere added
  2. customthe cooling bath was removed
  3. stirringthe mixture was stirred at room temperature overnight
  4. customThe dichloromethane was evaporated off
  5. filtrationfiltered
  6. washThe filtrate was washed with 1N HCl, water, aqueous bicarbonate and water
  7. dry with materialIt was then dried over Na2SO4
  8. customevaporated
  9. customIt was chromatographed over silica gel
  10. washThe pure decyl ester was eluted with ethylacetate-chloroform (1:4), 2.3 g m.p. 34°-35°

Quellen und Nachweise

ORD-Eintrag
ord-a2d6868564ac4e5fa674d173dbe62663
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762851

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