Hydrochloric Acid → HCID 67136343, compound

HRID 230909Notes

Reaction equation

HRID 230909 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:14]3[C:15]([O:19][C@@H:20]4[O:37][C@H:36]([CH2:38][O:39][C:40](=[O:42])[CH3:41])[C@@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:21]4[O:22][C:23](=[O:25])[CH3:24])=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:49][S:50](Cl)(=[O:52])=[O:51].Cl>ClCCl>[C:23]([O:22][C@@H:21]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@@H:36]([CH2:38][O:39][C:40](=[O:42])[CH3:41])[O:37][C@H:20]1[O:19][C:15]1[C:14]2[C:10]([CH2:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:50]([CH3:49])(=[O:52])=[O:51])=[CH:7][CH:6]=3)=[CH:11][O:12][C:13]=2[CH:18]=[CH:17][CH:16]=1)(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67136458HCID 67136458, compound

Product 1

HCID 67136343HCID 67136343, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-[2-(4-aminophenyl)ethyl]-4-hydroxybenzofuran (0.3 g) and 2,3,4,6-tetra-o-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (0.65 g) in dichloromethane (5 mL) was added borontrifluoride-diethyl ether complex (0.23 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: n-hexane/ethyl acetate=1/1-1/2-1/5) to give 3-[2-(4-aminophenyl)ethyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzofuran (0.36 g). To a solution of the obtained 3-[2-(4-aminophenyl)ethyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzofuran (50 mg) in dichloromethane (3 mL) were added pyridine (0.017 mL) and methanesulfonyl chloride (0.013 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by VARIAN BOND ELUT-SCX (eluent: methanol) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-[2-(4-methanesulfonylaminophenyl)ethyl]benzofuran (40 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. To the residue 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=8/1) to give the title compound (19 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by VARIAN BOND ELUT-SCX (eluent: methanol)

Sources & evidence

ORD record
ord-fa8a13c3fa0b441e97bd41cb0886e0ca
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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