Hydrochloric Acid → HCID 58786212, compound

HRID 1376005Notes

Reaction equation

HRID 1376005 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:24]([C@H:25]2[C@H:30]([OH:31])[C@@H:29]([OH:32])[C@H:28]([OH:33])[C@@H:27]([CH2:34][OH:35])[O:26]2)=[CH:23][CH:22]=[CH:21][C:5]=1[CH2:6][C:7]1[CH:16]=[C:15]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=[CH:14]2)[C:8]=1C(OC)=O.C(OCC)(=O)C.Cl>CO>[CH:8]1[C:9]2[C:15]([CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:16][C:7]=1[CH2:6][C:5]1[C:4]([F:3])=[C:24]([C@@H:25]2[O:26][C@H:27]([CH2:34][OH:35])[C@@H:28]([OH:33])[C@H:29]([OH:32])[C@H:30]2[OH:31])[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 58786118HCID 58786118, compound

Product 1

HCID 58786212HCID 58786212, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10% aqueous solution of sodium hydroxide (2 ml) was added to a solution of methyl 2-[2-fluoro-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]benzyl]azulene-1-carboxylate (19 mg) in methanol (2 ml). The mixture was refluxed with heating for 2 hours. The reaction mixture was neutralized by adding a 4 M ethyl acetate solution of hydrochloric acid and the solvent was evaporated under reduced pressure. Acetonitrile (5 ml) and a 4 M ethyl acetate solution of hydrochloric acid (1 ml) were added to the resulting residue and the mixture was refluxed with heating for 30 minutes. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-[3-(azulen-2-ylmethyl)-2-fluorophenyl]-D-glucitol (10 mg).

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 2 hours
  3. customthe solvent was evaporated under reduced pressure
  4. additionAcetonitrile (5 ml) and a 4 M ethyl acetate solution of hydrochloric acid (1 ml) were added to the resulting residue
  5. temperaturethe mixture was refluxed
  6. temperaturewith heating for 30 minutes
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-7ffca67d072643ec9834eda281824a5a
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

Loading…