HCID 136005304, compound → HCID 15887296, compound

HRID 2289086Notes

Reaction equation

HRID 2289086 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[N:22][O:23]C(=O)C)[CH2:20][CH3:21])=[C:15](O)[C:14]=1[CH2:28][CH2:29][CH3:30]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]2[C:19]([CH2:20][CH3:21])=[N:22][O:23][C:15]=2[C:14]=1[CH2:28][CH2:29][CH3:30]

Participants

3

Reactant 1

HCID 136005304HCID 136005304, compound

Product 1

HCID 15887296HCID 15887296, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of methyl 3-chloro-4-(3-(2-propyl-3-hydroxy-4-(1-acetoxyiminopropyl)phenoxy)propylthio)phenylacetate (Step D; 6.19 grams) in dry pyridine (65 mL) was refluxed for 3 hours. The solvent was removed in vacuo and the residue partitioned between isopropyl acetate and 0.1N HCl. The organic was washed once more with 0.1N HCl. The organic was dried over magnesium sulfate, filtered and evaporated to an oil. The crude product was placed on a slica gel column and eluted with hexane/CH2Cl2 (1:1) until the product appeared in the eluant. The mobile phase was changed to 100% CH2Cl2 and elution continued until all the title compound was recovered.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between isopropyl acetate and 0.1N HCl
  3. washThe organic was washed once more with 0.1N HCl
  4. dry with materialThe organic was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil
  7. washeluted with hexane/CH2Cl2 (1:1) until the product
  8. washThe mobile phase was changed to 100% CH2Cl2 and elution
  9. customwas recovered

Sources & evidence

ORD record
ord-60d857026aae4d339b6793bcaee5edef
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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