Oleic Acid → HCID 86682232, Verbindung

HRID 1479322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1479322
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][OH:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[C:15]([OH:34])(=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].Cl.C(N=C=N[CH2:41][CH2:42][CH2:43]N(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[C:15]([O:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][O:14][C:15](=[O:34])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])(=[O:34])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:43][CH2:42][CH3:41]

Komponenten

6

Edukt 3

HCID 445639Oleic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4360601N-Boc-diethanolamine

Produkt 1

HCID 86682232HCID 86682232, VerbindungAusbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-Butyl bis(2-hydroxyethyl)carbamate (Aldrich; 600 mg, 2.92 mmol) was dissolved in dichloromethane (30 mL), and stirred overnight at room temperature after adding oleic acid (Tokyo Chemical Industry Co., Ltd.; 1.82 g, 6.43 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.29 g, 6.72 mmol), and 4-dimethylaminopyridine (89 mg, 0.731 mmol). The aqueous layer was extracted with ethyl acetate after adding a saturated sodium bicarbonate aqueous solution to the reaction mixture. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure after filtration. The resulting residue was purified by silica gel column chromatography (hexane/chloroform=50/50 to 0/100) to give tert-butyl N,N-bis(2-((Z)-octadec-9-enoyloxy)ethyl)carbamate (1.26 g, 58.7%).

Aufarbeitung

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. additionafter adding a saturated sodium bicarbonate aqueous solution to the reaction mixture
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationafter filtration
  7. customThe resulting residue was purified by silica gel column chromatography (hexane/chloroform=50/50 to 0/100)

Quellen und Nachweise

ORD-Eintrag
ord-b3717de83ba8407183f7c9c86dc9a936
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09408914B2

Notizen zur Reaktion

Wird geladen…