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Diisopropylethylamine → N-[[1-[(2-Benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methioninal

HRID 1627490
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1627490
C(N(CC)C(C)C)(C)C.[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]1[C:19]([NH:21][C:22]1([C:28]([NH:30][C@H:31]([CH2:36][OH:37])[CH2:32][CH2:33][S:34][CH3:35])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:20]>CS(C)=O.C(Cl)Cl>[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[C:11]1[C:19]([NH:21][C:22]1([C:28]([NH:30][C@H:31]([CH:36]=[O:37])[CH2:32][CH2:33][S:34][CH3:35])=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 81531DiisopropylethylamineHCID 57672844N-[[1-[(2-Benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methioninol

Produkt 1

HCID 57672895N-[[1-[(2-Benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methioninal

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under an argon gas atmosphere, 245 mg (1.9 mmol) of N,N-diisopropylethylamine was added dropwise to a solution of 297 mg (1.9 mmol) of sulfur trioxide-pyridine complex in 10 ml of anhydrous dimethyl sulfoxide and 5 ml of anhydrous methylene chloride under ice-cooling, and the mixture was stirred for 15 minutes. Further, under ice-cooling, 100 mg (0.23 mmol) of N-[[1-[(2-benzothienylcarbonyl)amino]cyclohexyl]carbonyl]-L-methioninol was added to the reaction solution, and the mixture was stirred at the same temperature for 2 hours. The reaction solution was poured to ice-water, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with a 10% aqueous citric acid solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and after it was dried with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. 20 ml of diisopropyl ether was added to the residue, and the mixture was stirred at room temperature for 18 hours. The obtained crystal was collected by filtration to quantitatively obtain the title compound.

Aufarbeitung

  1. temperaturecooling
  2. temperatureFurther, under ice-cooling
  3. stirringthe mixture was stirred at the same temperature for 2 hours
  4. extractionthe mixture was extracted with ethyl acetate twice
  5. washThe organic layer was washed with a 10% aqueous citric acid solution
  6. dry with materiala saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and after it was dried with anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. addition20 ml of diisopropyl ether was added to the residue
  9. stirringthe mixture was stirred at room temperature for 18 hours
  10. filtrationThe obtained crystal was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d485975445f6448f93fd44657105a879
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08785631B2

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