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

HRID 230918Notes

Reaction equation

HRID 230918 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[C:16]3[C:17]([OH:21])=[CH:18][CH:19]=[CH:20][C:15]=3[O:14][CH:13]=2)=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[C:22]([O:25][C@@H:26]1[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:37]([O:43][C:44](=[O:46])[CH3:45])[C@@H:36]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:35][C@@H:27]1OC(=N)C(Cl)(Cl)Cl)(=[O:24])[CH3:23].C(=O)([O-])O.[Na+]>ClCCl>[C:22]([O:25][C@@H:26]1[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:37]([O:43][C:44](=[O:46])[CH3:45])[C@@H:36]([CH2:47][O:48][C:49](=[O:51])[CH3:50])[O:35][C@H:27]1[O:21][C:17]1[C:16]2[C:12]([CH2:11][CH2:10][C:7]3[CH:6]=[CH:5][C:4]([C:1](=[O:3])[NH2:2])=[CH:9][CH:8]=3)=[CH:13][O:14][C:15]=2[CH:20]=[CH:19][CH:18]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10896298alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)HCID 67135878HCID 67135878, compound

Product 1

HCID 671364964-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[2-(4-carbamoylphenyl)ethyl]benzofuranYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-[2-(4-carbamoylphenyl)ethyl]-4-hydroxybenzofuran (50 mg) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (96 mg) in dichloromethane (3 mL) was added borontrifluoride-diethyl ether complex (0.022 mL), and the mixture was stirred at room temperature overnight. 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: dichloromethane/methanol=20/1) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-[2-(4-carbamoylphenyl)ethyl]benzofuran (80 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 solvent was removed under reduced pressure. To the residue was added 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 treated with dichloromethane. The precipitated crystals were collected by filtration and dried under reduced pressure to give the title compound (13 mg).

Workup

  1. additionwas added borontrifluoride-diethyl ether complex (0.022 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: dichloromethane/methanol=20/1)

Sources & evidence

ORD record
ord-17a896a82c554bdc995c958759b1275f
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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