Dodecanoyl chloride → HCID 10161285, compound

HRID 460422Notes

Reaction equation

HRID 460422 reaction equation
[C@@H:1]1([O:12][C:13]2[CH:18]=[CH:17][C:16](N)=[CH:15][CH:14]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[C:20](Cl)(=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C([N:36](CC)CC)C>O1CCCC1>[C@@H:1]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:36][C:20](=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

5

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 887024-Aminophenyl glucoside

Product 1

HCID 10161285HCID 10161285, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The p-aminophenol-β-D-glucopyranoside (250 mg) thus obtained was dissolved in tetrahydrofuran (20 ml), and lauroyl chloride (300 mg) and triethylamine (1.0 g) were added. The reaction mixture was refluxed for 5 hours. The reaction solution was filtered to remove solids, and the filtrate was evaporated under vacuum to give a dry solid. The residue was purified by silica gel chromatography using a tetrahydrofuran/chloroform mixed solvent (1/1, volume ratio) as an eluant, and dodecanoylaminophenol-β-D-glucopyranoside was thus obtained.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. filtrationThe reaction solution was filtered
  3. customto remove solids
  4. customthe filtrate was evaporated under vacuum
  5. customto give a dry solid
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-22bd018553ba46428c39433f1fcc5ca4
Source dataset
uspto-grants-2007_03
Patent number
US07196178B2

Reaction notes

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