Ethanolamine → HCID 67136176, compound

HRID 230897Notes

Reaction equation

HRID 230897 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:30]2[C:31]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH2:43][CH2:44][CH2:45]OS(C)(=O)=O)=[CH:38][CH:37]=3)=[CH:32][O:33][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=O)C.[NH2:51][CH2:52][CH2:53][OH:54].[I-].[Na+]>C(#N)C.C(O)C>[C@@H:6]1([O:24][C:25]2[C:30]3[C:31]([CH2:34][CH2:35][C:36]4[CH:37]=[CH:38][C:39]([O:42][CH2:43][CH2:44][CH2:45][NH:51][CH2:52][CH2:53][OH:54])=[CH:40][CH:41]=4)=[CH:32][O:33][C:29]=3[CH:28]=[CH:27][CH:26]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 5238Sodium IodideHCID 86608856HCID 86608856, compound

Product 1

HCID 67136176HCID 67136176, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(2-[4-(3-hydroxypropoxy)phenyl]ethyl)benzofuran (0.23 g) and triethylamine (0.1 mL) in dichloromethane (6 mL) was added methanesulfonyl chloride (0.042 mL) under ice-cooling, and the mixture was stirred at room temperature 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 water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(2-{(4-[3-(methanesulfonyloxy)propoxy]phenyl}ethyl)benzofuran (0.25 g). The obtained 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(2-{4-[3-(methanesulfonyloxy)propoxy]phenyl}ethyl)benzofuran (30 mg) was dissolved in acetonitrile (0.5 mL)-ethanol (0.5 mL). To the solution were added 2-aminoethanol (0.025 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at 60° C. for 3 days. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (3 mL). To the solution was added sodium methoxide (28% methanol solution, 0.04 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (15 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methanol (3 mL)
  3. additionTo the solution was added sodium methoxide (28% methanol solution, 0.04 mL)
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. distillationthe residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)

Sources & evidence

ORD record
ord-f0a1d756d82849e3b603ab473da5cdae
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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