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

HRID 1927765Notes

Reaction equation

HRID 1927765 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:31]=[CH:30][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[CH2:28][CH3:29])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1.O.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[CH2:28][CH3:29])=[CH:30][CH:31]=2)=[O:10])=[CH:32][CH:33]=1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 68466862Ethyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-ethylphenyl)acetate

Product 1

HCID 594032252-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-ethylphenyl)acetic acidYield 21.3%

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-ethylphenyl)acetate (10 mg, 0.0215 mmol) was diluted with dioxane (500 μL) followed by the addition of NaOH (0.0429 ml, 0.215 mmol) and 5 drops of water. After stirring for 3 hours, the reaction was diluted with ethyl acetate and 2N HCl, and the layers were separated. The organic layer was dried over MgSO4, filtered and concentrated. The crude material was purified by silica gel chromatography eluting with 10% MeOH/DCM to yield 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-ethylphenyl)acetic acid (2 mg, 21.3% yield). (400 MHz, CD3Cl3, CD3OD) 7.65 (d, 2H), 7.30 (d, 2H), 7.10-7.25 (m, 4H), 6.90 (m, 3H), 3.62 (m, 2H), 3.40 (s, 1H), 2.90 (t, 2H), 2.55 (q, 2H), 1.15 (t, 3H).

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel chromatography
  6. washeluting with 10% MeOH/DCM

Sources & evidence

ORD record
ord-c089359cfbc74b1480f94d1e2e68b060
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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