Sodium Bicarbonate → 3-[2-(4-acetylaminophenyl)ethyl]-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)benzofuran

HRID 230907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230907
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[C:17]3[C:18]([OH:22])=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][CH:14]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:23]([O:26][C@@H:27]1[C@@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@H:38]([O:44][C:45](=[O:47])[CH3:46])[C@@H:37]([CH2:48][O:49][C:50](=[O:52])[CH3:51])[O:36][C@@H:28]1OC(=N)C(Cl)(Cl)Cl)(=[O:25])[CH3:24].C(=O)([O-])O.[Na+]>ClCCl>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][C:13]2[C:17]3[C:18]([O:22][C@@H:28]4[O:36][C@H:37]([CH2:48][O:49][C:50](=[O:52])[CH3:51])[C@@H:38]([O:44][C:45](=[O:47])[CH3:46])[C@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@H:27]4[O:26][C:23](=[O:25])[CH3:24])=[CH:19][CH:20]=[CH:21][C:16]=3[O:15][CH:14]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 10896298alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)HCID 671358873-[2-(4-Acetylaminophenyl)ethyl]-4-hydroxybenzofuran

Produkt 1

HCID 671359763-[2-(4-acetylaminophenyl)ethyl]-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)benzofuranAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 3-[2-(4-acetylaminophenyl)ethyl]-4-hydroxybenzofuran (30 mg) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (64 mg) in dichloromethane (3 mL) was added boron trifluoride-diethyl ether complex (0.013 mL), and the mixture was stirred at room temperature for three days. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethylacetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/3-1/2) to give 3-[2-(4-acetylaminophenyl)ethyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzofuran (38 mg). This material was dissolved in methanol (3 mL). To the solution was added sodium methoxide (28% methanol solution, 0.02 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=6/1) to give the title compound (12 mg).

Aufarbeitung

  1. additionwas added boron trifluoride-diethyl ether complex (0.013 mL)
  2. extractionthe resulting mixture was extracted with ethylacetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/3-1/2)

Quellen und Nachweise

ORD-Eintrag
ord-1406a09dc9f44544a782f676b7547eb6
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566699B2

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