1,4-Dioxane → HCID 68783179, compound

HRID 2266536Notes

Reaction equation

HRID 2266536 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([NH2:13])[CH:7]=1.C[O:16][C:17](=O)[CH:18]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1)[C:19](=O)[CH2:20][CH3:21].O1CCOCC1.C([O-])(=O)C.[Na+]>O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:7]=1[C:17](=[O:16])[C:18]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:28][CH:29]=1)=[C:19]([CH2:20][CH3:21])[NH:13]2

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 517045Sodium AcetateHCID 66717607(3-Amino-4-fluorophenoxy)acetic acid methyl esterHCID 68783429HCID 68783429, compound

Product 1

HCID 68783179HCID 68783179, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (3-amino-4-fluorophenoxy)acetic acid methyl ester (1.0 g), 2-(4-methanesulfonylbenzyl)-3-oxopentanoic acid methyl ester (1.4 g), polyphosphoric acid (5 mL) and dioxane (20 mL) was heated at 130° C. for 17 hours. The mixture was cooled to room temperature, diluted with water and the pH adjusted to 4 by the addition of sodium acetate. The mixture was extracted with ethyl acetate and the combined extracts dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound as a honey coloured gum, 2.3 g.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe combined extracts dried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d9290902dff4402aa51f7fc39a50c55f
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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