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Chlorotrimethylsilane → (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-2-methoxy-6-(trimethylsilyloxymethyl)tetrahydropyran-3,4,5-triol

HRID 1912990
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1912990
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([O:19][CH3:20])[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([F:30])[C:23]=1[F:31].[CH3:32][Si:33]([CH3:36])([CH3:35])Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([O:19][CH3:20])[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][O:18][Si:33]([CH3:36])([CH3:35])[CH3:32])[O:9]2)=[CH:4][C:3]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([F:30])[C:23]=1[F:31]
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Komponenten

5

Edukt 2

HCID 6397ChlorotrimethylsilaneHCID 86685109(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Produkt 1

HCID 86685110(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-2-methoxy-6-(trimethylsilyloxymethyl)tetrahydropyran-3,4,5-triolAusbeute 107,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 1049PyridineLösungsmittel

Versuchsvorschrift

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 2g (1.31 g, 2.84 mmol) was dissolved in 15 mL pyridine, followed by addition of 4-dimethylamino pyridine (70 mg, 0.57 mmol) and trimethyl-chloro-silane (514 mg, 3.4 mmol). The reaction mixture was stirred for 16 hours and then concentrated under reduced pressure. The resulting residue was dissolved in 150 mL ethyl acetate and washed with pyridine (50 mL×2), water (30 mL) and saturated sodium chloride solution (30 mL) in turn. The organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-2-methoxy-6-(trimethylsilyloxymethyl)tetrahydropyran-3,4,5-triol 2h (1.63 g, pale yellow solid), yield: 100%.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in 150 mL ethyl acetate
  3. washwashed with pyridine (50 mL×2), water (30 mL) and saturated sodium chloride solution (30 mL) in turn
  4. extractionThe organic extract
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b9ad58315f97432082a56e155aeaf4b9
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08609622B2

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