1,1'-Carbonyldiimidazole → N-(4-iso-propylbenzenesulfonyl)-alpha-(4-tert-butyldimethylsilyloxymethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamide

HRID 865528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 865528
[Si:1]([O:8][CH2:9][C:10]1[CH:29]=[CH:28][C:13]([O:14][CH:15]([C:19]2[CH:24]=[CH:23][C:22]3[O:25][CH2:26][O:27][C:21]=3[CH:20]=2)[C:16]([OH:18])=O)=[C:12]([CH2:30][CH2:31][CH3:32])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:45]([C:48]1[CH:53]=[CH:52][C:51]([S:54]([NH2:57])(=[O:56])=[O:55])=[CH:50][CH:49]=1)([CH3:47])[CH3:46].N12CCCN=C1CCCCC2>C1COCC1.CCOC(C)=O>[CH:45]([C:48]1[CH:49]=[CH:50][C:51]([S:54]([NH:57][C:16](=[O:18])[CH:15]([C:19]2[CH:24]=[CH:23][C:22]3[O:25][CH2:26][O:27][C:21]=3[CH:20]=2)[O:14][C:13]2[CH:28]=[CH:29][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:11][C:12]=2[CH2:30][CH2:31][CH3:32])(=[O:55])=[O:56])=[CH:52][CH:53]=1)([CH3:47])[CH3:46]

Komponenten

7

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2323144-(1-Methylethyl)benzenesulfonamideHCID 19080469alpha-(4-Tert-butyldimethylsilyloxymethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetic acid

Produkt 1

HCID 19080371N-(4-iso-propylbenzenesulfonyl)-alpha-(4-tert-butyldimethylsilyloxymethyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetamideAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3.30 g (7.21 mmol) of the crude product from Step C dissolved in 40 mL of anhydrous THF was added 1.75 g (10.8 mmol) of 1,1'-carbonyldiimidazole and the reaction mixture was magnetically stirred and heated at reflux for 10 minutes. The reaction was then cooled to room temperature, 2.15 g (10.8 mmol) of 4-iso-propylbenzenesulfonamide and 1.61 mL (10.8 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added and the reaction was stirred for an additional 30 minutes at room temperature. The mixture was then diluted with EtOAc (80 mL), washed with 10% aqueous citric acid, saturated aqueous NaCl, dried (MgSO4), filtered and evaporated. The residue was partially purified on a silica gel flash chromatography column eluted with CHCl3 --MeOH--NH4OH (92:8:0.5). The semi-purified material was combined and repurified on a second silica gel flash chromatography column eluted initially with 35% EtOAc-hexane, later with 50% EtOAc-hexane, and finally with 70% EtOAc-hexane. Combination of the purified fractions and evaporation afforded 3.20 g (69%) of the title compound as a yellow oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 10 minutes
  3. stirringthe reaction was stirred for an additional 30 minutes at room temperature
  4. washwashed with 10% aqueous citric acid, saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was partially purified on a silica gel flash chromatography column
  9. washeluted with CHCl3 --MeOH--NH4OH (92:8:0.5)
  10. customrepurified on a second silica gel flash chromatography column
  11. washeluted initially with 35% EtOAc-hexane, later with 50% EtOAc-hexane
  12. customCombination of the purified fractions and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-d9e41486627f4b73ac84b2ad3b2e224d
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565485

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