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

HRID 230907Notes

Reaction equation

HRID 230907 reaction equation
[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]

Participants

5

Reactant 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

Product 1

HCID 671359763-[2-(4-acetylaminophenyl)ethyl]-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)benzofuranYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1406a09dc9f44544a782f676b7547eb6
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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