Hydrochloric Acid → N-[[1-[[(E)-3-(2-furanyl)-1-oxo-2-Propenyl]amino]cyclohexyl]carbonyl]-L-methionine

HRID 1627498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1627498
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]1C(=O)[C:11](=[O:14])[C:10]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[N:9]=1.[NH2:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][CH2:23][S:24][CH3:25].C(OCC)(=[O:31])C.Cl>CN1CCOCC1.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]([NH:9][C:10]1([C:11]([NH:20][C@H:21]([C:26]([OH:28])=[O:27])[CH2:22][CH2:23][S:24][CH3:25])=[O:14])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)=[O:31]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6137L-MethionineHCID 8857Ethyl AcetateHCID 67180194HCID 67180194, Verbindung

Produkt 1

HCID 24737876N-[[1-[[(E)-3-(2-furanyl)-1-oxo-2-Propenyl]amino]cyclohexyl]carbonyl]-L-methionineAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 79724-MethylmorpholineLösungsmittel

Versuchsvorschrift

A solution of 491 mg (2 mmol) of 2-[(E)-2-(2-furanyl)ethenyl]-3-oxo-1-azaspiro[4.5]dec-1-en-4-one and 597 mg (4 mmol) of L-methionine in 20 ml of N-methylmorpholine was heated under reflux for 15 hours. After ethyl acetate and water were added to the reaction solution, it was acidified using concentrated hydrochloric acid. The organic layer was separated and successively washed with water and saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography to obtain 74 mg (9%) of the title compound.

Aufarbeitung

  1. temperatureunder reflux for 15 hours
  2. customThe organic layer was separated
  3. washsuccessively washed with water and saturated brine
  4. dry with materialby drying with anhydrous sodium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-28a9ebc1eb3a46569a2b5b92249059b1
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785631B2

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