Hydrochloric Acid → HCID 58786115, compound

HRID 1376002Notes

Reaction equation

HRID 1376002 reaction equation
[OH-].[Na+].[C@@H:3]1([C:14]2[CH:15]=[C:16]([CH2:26][C:27]3[CH:36]=[C:35]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=[CH:34]4)[C:28]=3C(OC)=O)[C:17]3[C:22]([C:23]=2[O:24][CH3:25])=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@H:4]1[OH:5].Cl>CO>[CH:28]1[C:29]2[C:35]([CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:36][C:27]=1[CH2:26][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]([O:24][CH3:25])=[C:14]([C@@H:3]2[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@H:4]2[OH:5])[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58786200HCID 58786200, compound

Product 1

HCID 58786115HCID 58786115, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 M aqueous solution of sodium hydroxide (12 ml) was added dropwise to a solution of methyl 2-[3-[(1S)-1,5-anhydro-D-glucitol-1-yl]-4-methoxy-1-naphthyl]methylazulene-1-carboxylate (0.23 g) in methanol (8.0 ml) and the mixture was refluxed with heating for three hours. A 1 M aqueous solution of hydrochloric acid (12 ml) was added to the reaction mixture under cooling with ice and the solvent was evaporated. The resulting residue was suspended in acetonitrile (15 ml). A 4 M 1,4-dioxane solution of hydrochloric acid (0.4 ml) was added dropwise to the suspension and the mixture was refluxed with heating for 15 minutes. The insoluble matter was removed by filtration and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography and reverse phase column chromatography in that order to obtain (1S)-1,5-anhydro-1-[4-(azulen-2-ylmethyl)-1-methoxy-2-naphthyl]-D-glucitol (0.08 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for three hours
  3. temperatureunder cooling with ice
  4. customthe solvent was evaporated
  5. additionA 4 M 1,4-dioxane solution of hydrochloric acid (0.4 ml) was added dropwise to the suspension
  6. temperaturethe mixture was refluxed
  7. temperaturewith heating for 15 minutes
  8. customThe insoluble matter was removed by filtration
  9. customthe solvent was evaporated
  10. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6a7a79f745604495b89185169130ff70
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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