Potassium Carbonate → (5RS)-3-(3-Fluoro-4-thiomorpholin-4-yl phenyl)-5-(1,2,3-triazol-1-ylmethyl)-4,5-dihydroisoxazole

HRID 1793849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1793849
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1F.C(=O)([O-])[O-].[K+].[K+].[NH:26]1[CH2:31][CH2:30][S:29][CH2:28][CH2:27]1>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[N:26]1[CH2:31][CH2:30][S:29][CH2:28][CH2:27]1

Komponenten

4

Edukt 3

HCID 11430Potassium CarbonateHCID 67164ThiomorpholineHCID 11334553HCID 11334553, Verbindung

Produkt 1

HCID 9946232(5RS)-3-(3-Fluoro-4-thiomorpholin-4-yl phenyl)-5-(1,2,3-triazol-1-ylmethyl)-4,5-dihydroisoxazole

Versuchsvorschrift

A mixture of (5RS)-3-(3,4-difluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-4,5-dihydroisoxazole (528 mg, 2 mM), potassium carbonate (414 mg, 3 mM), and thiomorpholine (7.5 ml) was heated under nitrogen at 130° for 40 hours. After cooling, the mixture was partitioned between water (150 ml) and ethyl acetate (150 ml). The organic extract was washed with aqueous sodium dihydrogen phosphate (75 ml), sodium bicarbonate (75 ml), and brine (75 ml). After drying (magnesium sulfate) and evaporation, the crude product was then purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient from 50–100% ethyl acetate in isohexane. Relevant fractions were combined to give the desired product (305 mg).

Aufarbeitung

  1. temperaturewas heated under nitrogen at 130° for 40 hours
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between water (150 ml) and ethyl acetate (150 ml)
  4. extractionThe organic extract
  5. washwas washed with aqueous sodium dihydrogen phosphate (75 ml), sodium bicarbonate (75 ml), and brine (75 ml)
  6. customAfter drying
  7. custom(magnesium sulfate) and evaporation
  8. customthe crude product was then purified by chromatography on a 20 g silica Mega Bond Elut® column
  9. washeluting with a gradient from 50–100% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-f2b05b78100b40d998b430c978fd727f
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022705B2

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