Hydrochloric Acid → HCID 58786227, compound

HRID 1375995Notes

Reaction equation

HRID 1375995 reaction equation
[CH3:1][O-:2].[Na+].Cl[CH2:5][C:6]1[CH:7]=[C:8]([CH:24]=[C:25]([C@H:27]2[C@H:32]([OH:33])[C@@H:31]([OH:34])[C@H:30]([OH:35])[C@@H:29]([CH2:36][OH:37])[O:28]2)[CH:26]=1)[CH2:9][C:10]1[CH:19]=[C:18]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17]2)[C:11]=1C(OC)=O.[OH-].[Na+].Cl>CO>[CH:19]1[C:18]2[C:12]([CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:11][C:10]=1[CH2:9][C:8]1[CH:24]=[C:25]([C@@H:27]2[O:28][C@H:29]([CH2:36][OH:37])[C@@H:30]([OH:35])[C@H:31]([OH:34])[C@H:32]2[OH:33])[CH:26]=[C:6]([CH2:5][O:2][CH3:1])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 58786195HCID 58786195, compound

Product 1

HCID 58786227HCID 58786227, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

28% methanol solution of sodium methoxide (0.5 ml) was added to a solution of methyl 2-[3-(chloromethyl)-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yl]benzyl]azulene-1-carboxylate (0.06 g) in methanol (3.0 ml) at room temperature. The mixture was stirred for one hour. 10% aqueous solution of sodium hydroxide (3.0 ml) was further added to the reaction mixture and the mixture was refluxed with heating for one hour. After cooling to room temperature, the reaction mixture was neutralized by adding 10% aqueous solution of hydrochloric acid, extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-[3-(azulen-2-ylmethyl)-5-(methoxymethyl)phenyl]-D-glucitol (0.02 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for one hour
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-de1d8617c87748d6adb18a4bbdcfbca7
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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