Hydrochloric Acid → 2-(4-ethoxy-3-[(2S,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylic acid

HRID 1375993Notes

Reaction equation

HRID 1375993 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:26]=[CH:25][C:9]([CH2:10][C:11]2[CH:20]=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:21]([O:23]C)=[O:22])=[CH:8][C:7]=1[C@H:27]1[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:31]([O:37][C:38](=[O:40])[CH3:39])[C@H:30]([O:41][C:42](=[O:44])[CH3:43])[C@@H:29]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[O:28]1)[CH3:4].Cl>CO>[CH2:3]([O:5][C:6]1[CH:26]=[CH:25][C:9]([CH2:10][C:11]2[CH:20]=[C:19]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18]3)[C:12]=2[C:21]([OH:23])=[O:22])=[CH:8][C:7]=1[C@H:27]1[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:31]([O:37][C:38](=[O:40])[CH3:39])[C@@H:30]([O:41][C:42](=[O:44])[CH3:43])[C@@H:29]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[O:28]1)[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58786173methyl 2-(4-ethoxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylate

Product 1

HCID 693824782-(4-ethoxy-3-[(2S,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylic acidYield 70.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10% aqueous solution of sodiumhydroxide (5.0 ml) was added dropwise to a solution of methyl 2-(4-ethoxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy) methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylate (0.58 g) in methanol (5.0 ml) at room temperature. The mixture was stirred for 30 minutes and refluxed with heating for further six hours. After cooling with ice, the reaction mixture was neutralized by adding 10% aqueous solution of hydrochloric acid. The neutralized product was 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 2-(4-ethoxy-3-[(2S,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylic acid (0.4 g).

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for further six hours
  3. temperatureAfter cooling with ice
  4. extractionThe neutralized product was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-3b96519c882a47f1acbc8574c92c8c0c
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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