Potassium Carbonate → (9-(4-(2-Hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

HRID 446421

Reaktionsgleichung

Reaktionsgleichung von HRID 446421
C(=O)([O-])[O-].[K+].[K+].FC(F)(F)C(O)=O.[CH:14]([C:17]1[S:18][CH:19]=[C:20]([C:22]([N:24]2[CH2:29][C:28]3([CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[O:27][CH2:26][CH2:25]2)=[O:23])[N:21]=1)([CH3:16])[CH3:15].CS([O:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][CH2:49]O)=[CH:44][CH:43]=1)(=O)=O>C(#N)C.O>[OH:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][CH2:49][N:32]2[CH2:31][CH2:30][C:28]3([O:27][CH2:26][CH2:25][N:24]([C:22]([C:20]4[N:21]=[C:17]([CH:14]([CH3:16])[CH3:15])[S:18][CH:19]=4)=[O:23])[CH2:29]3)[CH2:34][CH2:33]2)=[CH:44][CH:43]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 581685974-(2-Hydroxyethyl)phenethyl methanesulfonate2×HCID 66964182(2-Isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

Produkt 1

HCID 58168559(9-(4-(2-Hydroxyethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Potassium carbonate (0.634 g) was added to a solution of (2-isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate [Example 1, step b] (0.971 g) and 4-(2-hydroxyethyl)phenethyl methanesulfonate [Aromatic Intermediate 10] (0.56 g) in acetonitrile (20 mL) and water (0.3 mL). The reaction mixture was heated at 60° C. for 1 day. The solvent was evaporated under reduced pressure and the residue partitioned between water and ethyl acetate. The aqueous layer was re-extracted with ethyl acetate and the combined organic phases were dried, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography, using 2% methanol in dichloromethane with 1% triethylamine as solvent. Fractions containing the product were evaporated to dryness to afford the subtitled compound. Yield 0.68 g.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was re-extracted with ethyl acetate
  4. customthe combined organic phases were dried
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by flash silica chromatography
  8. additionFractions containing the product
  9. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b83e372cccba429ba151f23b5172a758
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476265B2

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