Sodium Hydroxide → 2-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-methoxyphenyl)acetic acid

HRID 453556Notes

Reaction equation

HRID 453556 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:30]=[CH:29][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25]C)=[O:24])=[CH:18][C:17]=3[O:27][CH3:28])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][C:17]=3[O:27][CH3:28])=[CH:29][CH:30]=2)=[O:10])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68464709Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-methoxyphenyl)acetate

Product 1

HCID 594031542-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-methoxyphenyl)acetic acidYield 65.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-(4-((4-chlorophenethyl) carbamoyl)phenoxy)-3-methoxyphenyl)acetate (0.065 g, 0.143 mmol) in methanol/THF (1:1, 3 ml) was added NaOH (0.100 ml, 0.500 mmol). After 5 minutes, reaction was quenched with 10 ml of 2N HCl and the product was extracted into ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The crude material was purified by silica gel chromatography, eluting with a gradient of 0.5% methanol/dichloromethane (containing 0.5% AcOH) to 7.5% methanol/dichloromethane containing (0.5% AcOH) to provide 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-methoxyphenyl)acetic acid (0.041 g, 65.1% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.37-8.41 (bt, NH), 7.70 (d, J=8.7 Hz, 2H), 7.28 (d, J=8.6 Hz, 2H), 7.23 (d, J=8.5 Hz, 2H), 7.08 (s, 1H), 7.02 (d, J=8.6 Hz, 1H), 6.91 (d, J=8.6 Hz, 2H), 3.64 (s, 2H), 3.56 (t, J=6.8 Hz, 2H), 2.88 (t, J=7.4 Hz, 2H).

Workup

  1. customreaction
  2. customwas quenched with 10 ml of 2N HCl
  3. extractionthe product was extracted into ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with a gradient of 0.5% methanol/dichloromethane (containing 0.5% AcOH) to 7.5% methanol/dichloromethane containing (0.5% AcOH)

Sources & evidence

ORD record
ord-84db9a32666d48029cffba50b72bc2d3
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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