Ethyl Acetate → (E)-methyl 4-(2-(2-(tert-butoxycarbonyl)ethoxy)ethylamino)-4-oxobut-2-enoate

HRID 926904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926904
NCCOCCN[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[C:15]([O:22][CH3:23])(=[O:21])/[CH:16]=[CH:17]/[C:18]([O-:20])=O.CCN=C=NC[CH2:30][CH2:31][N:32](C)C.[CH3:35][CH2:36][O:37]C(C)=O>CC#N>[C:10]([O:9][C:8]([CH2:35][CH2:36][O:37][CH2:30][CH2:31][NH:32][C:18](=[O:20])/[CH:17]=[CH:16]/[C:15]([O:22][CH3:23])=[O:21])=[O:14])([CH3:11])([CH3:12])[CH3:13]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 12106198tert-Butyl [2-(2-aminoethoxy)ethyl]carbamateHCID 21721168(E)-4-methoxy-4-oxobut-2-enoate

Produkt 1

HCID 86655429(E)-methyl 4-(2-(2-(tert-butoxycarbonyl)ethoxy)ethylamino)-4-oxobut-2-enoateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (1.0 g, 4.90 mmol) was then taken up in 20 mL of CH3CN along with mono methyl fumarate (637 mg, 4.90 mmol) and EDCI (1.7 g, 5.39 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc (20 mL), washed with saturated aqueous NaHCO3, brine, dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (9:1 CH2Cl2/MeOH) to afford 1.0 g of (E)-methyl 4-(2-(2-(tert-butoxycarbonyl)ethoxy)ethylamino)-4-oxobut-2-enoate (64% yield). MS (EI) called for C14H24 N2O6: 316.16; found 317 (M+1).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washwashed with saturated aqueous NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (9:1 CH2Cl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-a0ff1f8d2e6940408a9a4abbf4ed772f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09289503B2

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