Water → 2-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-methylphenyl)acetic acid

HRID 1927753Notes

Reaction equation

HRID 1927753 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]CC)=[O:24])=[CH:18][C:17]=3[CH3:28])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].O>O1CCOCC1.C(OCC)(=O)C.Cl>[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[CH3:28])=[CH:29][CH:30]=2)=[O:10])=[CH:31][CH:32]=1

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68469001Ethyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-methylphenyl)acetate

Product 1

HCID 594032152-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-methylphenyl)acetic acidYield 85.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-methylphenyl)acetate (20 mg, 0.0443 mmol) was diluted with dioxane (500 μL) followed by the addition of NaOH (0.0885 ml, 0.443 mmol) and 200 μL of water. After stirring for 3 hours, the reaction was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-methylphenyl)acetic acid (16.0 mg, 85.3% yield). NMR (400 MHz, CD3Cl3, CD3OD) 7.62 (d, 2H), 7.30 (d, 2H), 7.10-7.22 (m, 4H), 6.92 (d, 1H), 6.85 (d, 2H), 3.65 (t, 2H), 3.60 (s, 2H), 2.90 (t, 2H), 2.15 (s, 3H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-42dc8e62fbd64b6b9beb7f79abda2c26
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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