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

HRID 453535Notes

Reaction equation

HRID 453535 reaction equation
[Cl:1][C:2]1[CH:41]=[CH:40][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:39]=[CH:38][C:14]([O:15][C:16]3[C:21]([C:22]4[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=4)=[CH:20][C:19]([CH2:32][C:33]([O:35]CC)=[O:34])=[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: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[C:21]([C:22]4[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=4)=[CH:20][C:19]([CH2:32][C:33]([OH:35])=[O:34])=[CH:18][CH:17]=3)=[CH:38][CH:39]=2)=[O:10])=[CH:40][CH:41]=1

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68467112Ethyl 2-(6-(4-(4-chlorophenethylcarbamoyl)phenoxy)-4'-(methylsulfonyl)biphenyl-3-yl)acetate

Product 1

HCID 594031712-(6-(4-(4-Chlorophenethylcarbamoyl)phenoxy)-4'-(methylsulfonyl)biphenyl-3-yl)acetic acidYield 52.5%

Reagents, catalysts & solvents 3

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

Procedure

Ethyl 2-(6-(4-(4-chlorophenethylcarbamoyl)phenoxy)-4′-(methylsulfonyl)biphenyl-3-yl)acetate (20 mg, 0.0338 mmol) was diluted with dioxane (1 mL) followed by the addition of NaOH (0.0676 ml, 0.338 mmol) and 300 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-(6-(4-(4-chlorophenethylcarbamoyl)phenoxy)-4′-(methylsulfonyl)biphenyl-3-yl)acetic acid (10 mg, 52.5% yield). (400 MHz, CD3Cl3, CD3OD) 7.90 (d, 2H), 7.70 (d, 2H), 7.60 (d, 2H), 7.40 (s, 1H), 7.35 (d, 1H), 7.25 (d, 2H), 7.15 (d, 2H), 7.05 (d, 1H), 6.85 (d, 2H), 6.55 (t, 1H), 3.63 (m, 4H), 3.05 (s, 3H), 2.90 (t, 2H).

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-c874085a553440258d96d32eb347dcf3
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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