Hydrochloric Acid → N-[(E,E)-4-ethyl-2,4-hexadienoyl]-L-threonine

HRID 35573

Reaktionsgleichung

Reaktionsgleichung von HRID 35573
[CH2:1](/[C:3](=[CH:16]\[CH3:17])/[CH:4]=[CH:5]/[C:6]([O:8]N1C(=O)CCC1=O)=O)[CH3:2].[NH2:18][C@H:19]([C:23]([OH:25])=[O:24])[C@@H:20]([CH3:22])[OH:21].C(N(CC)CC)C.Cl>O1CCCC1.CN(C)C=O.O>[CH2:1](/[C:3](=[CH:16]\[CH3:17])/[CH:4]=[CH:5]/[C:6]([NH:18][C@H:19]([C:23]([OH:25])=[O:24])[C@@H:20]([CH3:22])[OH:21])=[O:8])[CH3:2]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 6288L-ThreonineHCID 8471TriethylamineHCID 14329790N-[(E,E)-4-ethyl-2,4-hexadienoyloxy]succinimide

Produkt 1

HCID 86742403N-[(E,E)-4-ethyl-2,4-hexadienoyl]-L-threonineAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-[(E,E)-4-ethyl-2,4-hexadienoyloxy]succinimide (1.19 g) in a mixture of tetrahydrofuran (50 ml) and dimethylformamide (30 ml) was added a solution of L-threonine (2.38 g) and triethylamine (2.78 ml) in water (50 ml). The mixture was stirred at ambient temperature for 6 hours and then acidified with 1N hydrochloric acid. The resulting mixture was extracted with ethyl acetate, washed with water and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give N-[(E,E)-4-ethyl-2,4-hexadienoyl]-L-threonine (640 mg).

Aufarbeitung

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7f5eeb8f4a4e4cc5a67cdfebe04fa304
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767768

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