Hydrochloric Acid → HCID 68864738, compound

HRID 230910Notes

Reaction equation

HRID 230910 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.C[Si]([N:47]=[C:48]=[O:49])(C)C.O.Cl>O1CCCC1>[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][C:48]([NH2:47])=[O:49])=[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 962WaterHCID 70696Trimethylsilyl isocyanateHCID 67136458HCID 67136458, compound

Product 1

HCID 68864738HCID 68864738, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 tetrahydrofuran (2 mL) was added trimethylsilyl isocyanate (0.014 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added water (0.3 mL), and the mixture was stirred at 50° C. for 2 hours. 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-ureidophenyl)ethyl]-benzofuran (20 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 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: dichlorometane/methanol=5/1) to give the title compound (4 mg).

Workup

  1. stirringthe mixture was stirred at 50° C. for 2 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by VARIAN BOND ELUT-SCX (eluent: methanol)

Sources & evidence

ORD record
ord-8dfb046d060f4e8184ac2cd02cf4b264
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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