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Triethylamine → Methyl 6-(benzenesulphonylmethyl)-2-(3-t-butyoxycarbonylamino-prop-1-yn-1-yl)-3-(furan-3-yl)benzoate

HRID 2177793
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2177793
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15](OS(C(F)(F)F)(=O)=O)[C:14]([C:29]3[CH:33]=[CH:32][O:31][CH:30]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:34]([NH:41][CH2:42][C:43]#[CH:44])([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].C(N(CC)CC)C>C(#N)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:44]#[C:43][CH2:42][NH:41][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:14]([C:29]3[CH:33]=[CH:32][O:31][CH:30]=3)=[CH:13][CH:12]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 86677115Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate2×

Produkt 1

HCID 67107946Methyl 6-(benzenesulphonylmethyl)-2-(3-t-butyoxycarbonylamino-prop-1-yn-1-yl)-3-(furan-3-yl)benzoateAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysator
HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)-benzoate (Intermediate 123, 0.756 g), N-Boc-propargylamine (0.698 g), copper (I) iodide (0.014 g) and bis(triphenylphosphine)palladium(II)chloride (0.026 g) were added to a solution of triethylamine (0.152 g) in acetonitrile (10 ml) and the mixture was heated at 70° C., under nitrogen, for 17 hours. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and DCM with a gradient of 0-10%. After evaporation of the appropriate fractions, the resulting residue was triturated with diethyl ether and the solid was collected by filtration to give methyl 6-(benzenesulphonylmethyl)-2-(3-t-butyoxycarbonylaminoprop-1-yn-1-yl)-3-(furan-3-yl)benzoate (0.225 g) as a white solid.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and DCM with a gradient of 0-10%
  7. customAfter evaporation of the appropriate fractions
  8. customthe resulting residue was triturated with diethyl ether
  9. filtrationthe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0f7bebee290e4f3e9b7d8c0061fffb05
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09067905B2

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