4-Aminosalicylic Acid → HCID 17919667, compound

HRID 1883520Notes

Reaction equation

HRID 1883520 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:18]([CH2:36]S([O-])(=O)=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]C>CN(C=O)C>[CH2:36]([O:7][C:6](=[O:8])[C:5]1[C:4](=[CH:3][C:2]([NH2:1])=[CH:10][CH:9]=1)[OH:11])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]/[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 46494-Aminosalicylic AcidHCID 10796Cesium carbonateHCID 18935672HCID 18935672, compound

Product 1

HCID 17919667HCID 17919667, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

To a suspension of para-amino-salicyclic acid (PAS) (0.47 g, 31 mmol) and Cesium carbonate (0.98 g, 3.0 mmol) in 50 ml anhydrous DMF was added elaidylmesylate (1.0 g, 2.9 mmol) and the reaction mixture was stirred at ambient temperature for 60 hours and at 35° C. for 48 hours. The reaction mixture was extracted with ether and water, and the organic phase was washed with NaHCO3(aq) and water. The solvent was evaporated off and the residue was purified on acolumn of silica gel with heptane/CH2Cl2/AcOH/MeOH (85:15:2:2) as the solvent system. Product containing fractions was repurified (70:30:2:2) and homogenous fractions were evaporated to give 0.6 g (51%) of the title compound.

Workup

  1. extractionThe reaction mixture was extracted with ether and water
  2. washthe organic phase was washed with NaHCO3(aq) and water
  3. customThe solvent was evaporated off
  4. customthe residue was purified on acolumn of silica gel with heptane/CH2Cl2/AcOH/MeOH (85:15:2:2) as the solvent system
  5. additionProduct containing fractions
  6. customwas repurified (70:30:2:2) and homogenous fractions
  7. customwere evaporated

Sources & evidence

ORD record
ord-a32d30d6a5184e04ba508004c6931de2
Source dataset
uspto-grants-2004_07
Patent number
US06762175B2

Reaction notes

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