Sodium Bicarbonate → 4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-(2-{4-[1-amino-1-(benzyloxycarbonylimino)methyl]phenyl}ethyl)benzofuran

HRID 230915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230915
[NH2:1][C:2]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[C:26]3[C:27]([OH:31])=[CH:28][CH:29]=[CH:30][C:25]=3[O:24][CH:23]=2)=[CH:16][CH:15]=1)=[N:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[C:32]([O:35][C@@H:36]1[C@@H:48]([O:49][C:50](=[O:52])[CH3:51])[C@H:47]([O:53][C:54](=[O:56])[CH3:55])[C@@H:46]([CH2:57][O:58][C:59](=[O:61])[CH3:60])[O:45][C@@H:37]1OC(=N)C(Cl)(Cl)Cl)(=[O:34])[CH3:33].C(=O)([O-])O.[Na+]>ClCCl>[C:32]([O:35][C@@H:36]1[C@@H:48]([O:49][C:50](=[O:52])[CH3:51])[C@H:47]([O:53][C:54](=[O:56])[CH3:55])[C@@H:46]([CH2:57][O:58][C:59](=[O:61])[CH3:60])[O:45][C@H:37]1[O:31][C:27]1[C:26]2[C:22]([CH2:21][CH2:20][C:17]3[CH:18]=[CH:19][C:14]([C:2]([NH2:1])=[N:3][C:4]([O:6][CH2:7][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)=[O:5])=[CH:15][CH:16]=3)=[CH:23][O:24][C:25]=2[CH:30]=[CH:29][CH:28]=1)(=[O:34])[CH3:33]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 10896298alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)HCID 67136072HCID 67136072, Verbindung

Produkt 1

HCID 671363054-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-(2-{4-[1-amino-1-(benzyloxycarbonylimino)methyl]phenyl}ethyl)benzofuranAusbeute 77,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 3-(2-{4-[1-amino-1-(benzyloxycarbonylimino)methyl]phenyl}ethyl)-4-hydroxybenzofuran (30 mg) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (43 mg) in dichloromethane (3 mL) was added boron trifluoride-diethyl ether complex (0.009 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. 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=1/1-2/3) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(2-{4-[1-amino-1-(benzyloxycarbonylimino)methyl]phenyl}ethyl)benzofuran (42 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 1 hour. To the reaction mixture was added 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: dichloromethane/methanol=10/1) to give 3-(2-{4-[1-amino-1-(benzyloxycarbonylimino)methyl]phenyl}ethyl)-4-(β-D-glucopyranosyloxy)benzofuran (20 mg). This material was dissolved in methanol (3 mL). To the solution was added 10% palladium-carbon powder (10 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The insoluble material was removed by filtration. The solvent of the filtrate was removed under reduced pressure to give the title compound (13 mg).

Aufarbeitung

  1. additionwas added boron trifluoride-diethyl ether complex (0.009 mL)
  2. extractionthe resulting mixture was extracted with ethyl acetate
  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=1/1-2/3)

Quellen und Nachweise

ORD-Eintrag
ord-fc0c0117705e4c7fb27d235de4de37eb
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566699B2

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