Potassium Carbonate → HCID 57899210, Verbindung

HRID 1802780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802780
[CH3:1][C:2]1[C:6]([CH2:7][CH2:8]OS(C)(=O)=O)=[C:5]([CH3:14])[N:4]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[N:3]=1.[CH3:25][O:26][C:27](=[O:41])/[CH:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][C:33]([C@@H:36]2[CH2:40][CH2:39][CH2:38][NH:37]2)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C)C(=O)C>[CH3:25][O:26][C:27](=[O:41])/[CH:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][C:33]([C@@H:36]2[CH2:40][CH2:39][CH2:38][N:37]2[CH2:8][CH2:7][C:6]2[C:2]([CH3:1])=[N:3][N:4]([S:15]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)(=[O:17])=[O:16])[C:5]=2[CH3:14])=[CH:32][CH:31]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 57899232HCID 57899232, VerbindungHCID 57899282HCID 57899282, Verbindung

Produkt 1

HCID 57899210HCID 57899210, VerbindungAusbeute 60,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21187609acetonitrile N,N-dimethylacetamideLösungsmittel

Versuchsvorschrift

To a mixture of methanesulfonic acid 2-[3,5-dimethyl-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-ethyl ester (600 mg, 1.61 mmol) and (E)-3-((S)-4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester (317 mg, 1.37 mmol) in 10 mL acetonitrile-N,N-dimethylacetamide (3:1 v/v) was added potassium carbonate (334 mg, 2.42 mmol). The mixture was subjected to microwave irradiation for 15 minutes and the crude mixture was filtered through a plug of Celite, which was washed with dichloromethane. The combined filtrates were partially concentrated and partitioned between ethyl acetate and aqueous ammonium chloride solution. The organic layer was washed three times with the same salt solution, which was back extracted once. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to give a yellow oil, which was purified via silica gel column chromatography (0-50% ethyl acetate in heptane) to give ((E)-3-[4-((S)-1-{2-[3,5-dimethyl-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-ethyl}-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester (423 mg, 0.833 mmol, 52% yield) as a colorless solid.

Aufarbeitung

  1. customirradiation for 15 minutes
  2. filtrationthe crude mixture was filtered through a plug of Celite, which
  3. washwas washed with dichloromethane
  4. concentrationThe combined filtrates were partially concentrated
  5. custompartitioned between ethyl acetate and aqueous ammonium chloride solution
  6. washThe organic layer was washed three times with the same salt solution, which
  7. extractionwas back extracted once
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto give a yellow oil, which
  11. customwas purified via silica gel column chromatography (0-50% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-fa2d7eba3df442d0b83a640156d5842d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349883B2

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