Water → 2-(6-(4-(4-Chlorophenethylcarbamoyl)phenoxy)biphenyl-3-yl)acetic acid

HRID 1927757Notes

Reaction equation

HRID 1927757 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:35]=[CH:34][C:14]([O:15][C:16]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:20][C:19]([CH2:28][C:29]([O:31]CC)=[O:30])=[CH:18][CH:17]=3)=[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:37]=[CH:36][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:20][C:19]([CH2:28][C:29]([OH:31])=[O:30])=[CH:18][CH:17]=3)=[CH:34][CH:35]=2)=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68467426HCID 68467426, compound

Product 1

HCID 594032112-(6-(4-(4-Chlorophenethylcarbamoyl)phenoxy)biphenyl-3-yl)acetic acidYield 16.9%

Reagents, catalysts & solvents 3

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

Procedure

Ethyl 2-(6-(4-(4-chlorophenethylcarbamoyl)phenoxy)biphenyl-3-yl)acetate (10 mg, 0.0195 mmol) was diluted with dioxane (1 mL) followed by the addition of NaOH (0.0389 ml, 0.195 mmol) and 200 μL of water. After stirring for 2 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-(6-(4-(4-chlorophenethylcarbamoyl)phenoxy)biphenyl-3-yl)acetic acid (1.6 mg, 16.9% yield) as a white solid. MS ESI negative M−H=485.

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-7bb29976fcd0452fb1ac114998edbbe6
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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