Diisopropylethylamine → N-[[1-[(2-Furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valinol

HRID 73845

Reaktionsgleichung

Reaktionsgleichung von HRID 73845
C(N(CC)C(C)C)(C)C.[NH2:10][C@H:11]([CH2:15][OH:16])[CH:12]([CH3:14])[CH3:13].[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]1[O:26][C:25](=[O:27])[C:24]2([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[N:23]=1>C(Cl)Cl.C1(C)C=CC=CC=1>[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([NH:23][C:24]1([C:25]([NH:10][C@H:11]([CH2:15][OH:16])[CH:12]([CH3:14])[CH3:13])=[O:27])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 640993L-ValinolHCID 247399602-(2-Furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

Produkt 1

HCID 24876087N-[[1-[(2-Furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valinolAusbeute 74,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 8.81 ml (50.6 mmol) of N,N-diisopropylethylamine and 2.09 g (20.2 mmol) of L-valinol in 10 mL of methylene chloride was added to a solution of 3.71 g (16.9 mmol) of 2-(2-furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one in 100 ml of toluene, and the mixture was heated under reflux for 14 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine. The organic layer was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue, and the mixture was stirred overnight. The obtained crystal was collected by filtration to obtain 4.06 g (74.7%) of the title compound.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure, ethyl acetate
  4. additionwas added to the residue
  5. washthe mixture was washed with water
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionEthyl acetate was added to the residue
  9. filtrationThe obtained crystal was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-6405efd6ebeb41a4b29260cd120c5ea8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829209B2

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