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

HRID 869784

Reaktionsgleichung

Reaktionsgleichung von HRID 869784
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) calcd for C14H24N2O6: 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-2188da8053ff4171b02b559fec2ef915
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969354B2

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