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Cesium carbonate → Methyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoate

HRID 2177785
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2177785
[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]([O:38][C:39]([NH:41][CH2:42][CH2:43][NH2:44])=[O:40])([CH3:37])([CH3:36])[CH3:35].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([NH:44][CH2:43][CH2:42][NH:41][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])[C:14]([C:29]3[CH:33]=[CH:32][O:31][CH:30]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 187201N-BOC-ethylenediamineHCID 634876Binap, (A+-)-HCID 86677115Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate2×

Produkt 1

HCID 67108007Methyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoate
Ausbeute 45,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-(trifluoromethanesulphonyloxy)benzoate (Intermediate 123, 0.05 g), N-(t-butoxycarbonyl)ethylenediamine (0.048 g), palladium acetate (0.006 g), cesium carbonate (0.065 g) and (+/−)BINAP (0.034 g) in toluene (1.5 ml) was stirred and heated at 100° C., under nitrogen for 20 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 cyclohexane with a gradient of 10-35%, to give methyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoate (0.023 g) as a yellow gum.

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
  7. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-35%

Quellen und Nachweise

ORD-Eintrag
ord-a8269728bd714725a5877770542b4a11
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09067905B2

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