Hydrochloric Acid → HCID 58786126, compound

HRID 1375998Notes

Reaction equation

HRID 1375998 reaction equation
C[O-].[Na+].C([O:7][C@@H:8]1[C@@H:13]([O:14]C(=O)C)[C@H:12]([O:18]C(=O)C)[C@@H:11]([CH2:22][O:23]C(=O)C)[O:10][C@H:9]1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][C:34]2[CH:43]=[C:42]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=[CH:41]3)[C:35]=2[C:44](=[O:46])[CH3:45])[CH:28]=1)(=O)C.Cl>C1COCC1.CO>[OH:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([OH:18])[C@@H:11]([CH2:22][OH:23])[O:10][C@H:9]1[C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][CH:32]=1)[CH2:33][C:34]1[CH:43]=[C:42]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=[CH:41]2)[C:35]=1[C:44](=[O:46])[CH3:45]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 58786150HCID 58786150, compound

Product 1

HCID 58786126HCID 58786126, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Sodium methoxide (16 mg) was added to a solution of (2S,3S,4R,5R,6R)-2-[3-[(1-acetylazulen-2-yl)methyl]phenyl]-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-3,4,5-triyl triacetate (0.09 g) in THF-methanol (ratio: 1:1, 6.0 ml) at 0° C. and the mixture was stirred for two hours. After neutralizing with a cation exchange resin, the reaction mixture was added to 10% aqueous solution of hydrochloric acid under cooling with ice. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 1-(2-[3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]benzyl]azulen-1-yl)ethanone (0.06 g).

Workup

  1. temperatureunder cooling with ice
  2. filtrationAfter filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-e59b5b34d2a8449d86d98b2d6ece512b
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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