(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one → (5r)-3-[3-Fluoro-4-(1 (r,s)-oxo-3,6-dihydro-2h-thiopyran-4-yl)phenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723805
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:17][C@H:16]([CH2:18][N:19]4[CH:23]=[CH:22][N:21]=[N:20]4)[O:15][C:14]3=[O:24])=[CH:9][C:8]=2[F:25])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:27].[Na+]>CO.C(OCC)(=O)C.O>[F:25][C:8]1[CH:9]=[C:10]([N:13]2[CH2:17][C@H:16]([CH2:18][N:19]3[CH:23]=[CH:22][N:21]=[N:20]3)[O:15][C:14]2=[O:24])[CH:11]=[CH:12][C:7]=1[C:4]1[CH2:5][CH2:6][S:1](=[O:27])[CH2:2][CH:3]=1

Komponenten

6

Edukt 2

HCID 11302859(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-oneHCID 23667635Sodium periodate

Produkt 1

HCID 11451677(5r)-3-[3-Fluoro-4-(1 (r,s)-oxo-3,6-dihydro-2h-thiopyran-4-yl)phenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-oneAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(5R)-3-[4-(3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one (Example 83; 1.25 g, 3.5 mmol) was stirred in a mixture of methanol and ethyl acetate (1:1, 50 ml) at ambient temperature. Sodium periodate (0.93 g, 4.3 mmol) in water (10 ml) was added dropwise, and it was stirred for 18 hours. Precipitated salts were removed by filtration and solvents were removed under vacuum. The residue was chromatographed on silica gel, washing with 25% acetone in dichloromethane, then eluting with 5 to 7% methanol in dichloromethane to give the title product (1.152 g).

Aufarbeitung

  1. customPrecipitated salts were removed by filtration and solvents
  2. customwere removed under vacuum
  3. customThe residue was chromatographed on silica gel
  4. washwashing with 25% acetone in dichloromethane
  5. washeluting with 5 to 7% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-f752ca4ffba34a81b583cd02910d6f3d
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141583B2

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