Sodium hydride → (5RS)-3-(3-Fluoro-4-iodophenyl)-5-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)-4,5-dihydro-isoxazole

HRID 1793678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1793678
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14]OS(C)(=O)=O)[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[I:8].[H-].[Na+].C([N:25]1[CH:29]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH:28]=[CH:27][O:26]1)C=C>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][N:30]([C:29]3[CH:28]=[CH:27][O:26][N:25]=3)[C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[I:8]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 22022967N-Allyl-3-(t-Butoxycarbonylamino)isoxazoleHCID 22022974(5RS)-3-(3-Fluoro-4-iodophenyl)-5-methanesulfonyloxymethyl-4,5-dihydro-isoxazole

Produkt 1

HCID 69521876(5RS)-3-(3-Fluoro-4-iodophenyl)-5-(N-(t-butoxycarbonyl)isoxazol-3-ylaminomethyl)-4,5-dihydro-isoxazoleAusbeute 86,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (5RS)-3-(3-Fluoro-4-iodophenyl)-5-methanesulfonyloxymethyl-4,5-dihydroisoxazole (1.7 g, 4.26 mM) in dry N,N-dimethylformamide (40 ml) under nitrogen, was treated with sodium hydride (60% in oil, 0.205 g, 5.13 mM), and stirred for 5 minutes. N-Allyl-3-(t-Butoxycarbonylamino)isoxazole (0.86 g, 4.69 mM) was added, and the mixture heated at 60° for 18 hours. After cooling and dilution with water (200 ml), the mixture was extracted with ethyl acetate (3×100 ml), the extracts were washed with water (2×100 ml), brine (100 ml), dried (magnesium sulfate). The residue after evaporation was purified by chromatography on a 50 g silica Mega Bond Elut® column, eluting with a mixture of 25% ethyl acetate in isohexane. Relevant fractions were combined to give the desired product (1.61 g). MS (ESP): 488 (MH+) for C18H19FIN3O4

Aufarbeitung

  1. temperaturethe mixture heated at 60° for 18 hours
  2. temperatureAfter cooling
  3. extractiondilution with water (200 ml), the mixture was extracted with ethyl acetate (3×100 ml)
  4. washthe extracts were washed with water (2×100 ml), brine (100 ml)
  5. dry with materialdried (magnesium sulfate)
  6. customThe residue after evaporation
  7. customwas purified by chromatography on a 50 g silica Mega Bond Elut® column
  8. washeluting with a mixture of 25% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-4aabe63e35d642b59669397eee9790dc
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07081538B1

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