Hydrochloric Acid → HCID 58786190, compound

HRID 1376003Notes

Reaction equation

HRID 1376003 reaction equation
C(#N)C.Cl.[CH2:5]([O:7][C:8]1[C:27]([C@H:28]2[C@H:33]([OH:34])[C@@H:32]([OH:35])[C@H:31]([OH:36])[C@@H:30]([CH2:37][OH:38])[O:29]2)=[CH:26][C:11]([CH2:12][C:13]2[CH:22]=[C:21]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=[CH:20]3)[C:14]=2C(O)=O)=[CH:10][C:9]=1[O:39][CH3:40])[CH3:6]>C(OCC)(=O)C>[CH:14]1[C:15]2[C:21]([CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:22][C:13]=1[CH2:12][C:11]1[CH:10]=[C:9]([O:39][CH3:40])[C:8]([O:7][CH2:5][CH3:6])=[C:27]([C@@H:28]2[O:29][C@H:30]([CH2:37][OH:38])[C@@H:31]([OH:36])[C@H:32]([OH:35])[C@H:33]2[OH:34])[CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 6342AcetonitrileHCID 58786176HCID 58786176, compound

Product 1

HCID 58786190HCID 58786190, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Acetonitrile and a 4 M ethyl acetate solution (0.02 ml) of hydrochloric acid (5 ml) were added to 2-[4-ethoxy-3-methoxy-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yl]benzyl]azulene-1-carboxylic acid (50 mg) and the mixture was refluxed with heating for 10 minutes. A 4 M ethyl acetate solution (0.02 ml) of hydrochloric acid was further added to the reaction mixture and the mixture was refluxed with heating for 30 minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2-ethoxy-3-methoxyphenyl]-D-glucitol (42 mg).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 10 minutes
  3. temperaturethe mixture was refluxed
  4. temperaturewith heating for 30 minutes
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-36cbc14145374d7f8e9cf6835825e809
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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