N-Methyldiethanolamine → (E)-N-methacryloylbut-2-enamide

HRID 514668

Reaktionsgleichung

Reaktionsgleichung von HRID 514668
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.COC1C(OC)=C(OC)C=C(/[CH:46]=[CH:47]/[C:48]([N:50]2[C:55](=[O:56])[CH:54]=[CH:53][CH2:52]C2)=[O:49])C=1.CN(CCO)CCO>C1(C)C=CC=CC=1.C1COCC1>[C:48]([NH:50][C:55](=[O:56])/[CH:54]=[CH:53]/[CH3:52])(=[O:49])[C:47]([CH3:46])=[CH2:1]

Komponenten

7

Edukt 4

HCID 7767N-MethyldiethanolamineHCID 11776TriphenylphosphineHCID 637858PiperlongumineHCID 5363146Diisopropyl azodicarboxylate

Produkt 1

HCID 72205393(E)-N-methacryloylbut-2-enamideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Experimental Procedure: Triphenylphosphine (77.0 mg, 0.29 mmol) and DIAD (60.0 mg, 0.29 mmol) were dissolved to a 1:1 mixture of THF and toluene (2 mL); then mono-demethylated piperlongumine (40.0 mg, 0.13 mmol) was added. After 10 min, N-methyldiethanolamine (120 mg, 0.06 mmol) was added to the mixture; the reaction was stirred at room temperature for 3 h. At the end, the solvent was evaporated under vacuum. The crude product was purified by preparative TLC(CH2Cl2/MeOH=9/1) to afford the desired product in 78% yield.

Aufarbeitung

  1. customAt the end, the solvent was evaporated under vacuum
  2. customThe crude product was purified by preparative TLC(CH2Cl2/MeOH=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-7d2111e22d0e4127842d146bb6aaa038
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108923B2

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