Water → 2-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-(thiophen-2-yl)phenyl)acetic acid

HRID 1927755Notes

Reaction equation

HRID 1927755 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:34]=[CH:33][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[C:28]3[S:29][CH:30]=[CH:31][CH:32]=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:34]=[CH:33][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[C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:35][CH:36]=1

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68466786Ethyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-(thiophen-2-yl)phenyl)acetate

Product 1

HCID 594031572-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-(thiophen-2-yl)phenyl)acetic acidYield 37.4%

Reagents, catalysts & solvents 3

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

Procedure

Ethyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-(thiophen-2-yl)phenyl)acetate (20 mg, 0.038 mmol) was diluted with dioxane (500 μL) followed by the addition of NaOH (0.052 ml, 0.26 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-(thiophen-2-yl)phenyl)acetic acid (7 mg, 37% yield) as a white solid. 1H NMR (400 MHz, CD3Cl3, CD3OD) 7.69 (s, 1H), 7.64 (d, 2H), 7.45 (d, 1H), 7.30 (d, 2H), 7.22 (d, 1H), 7.15 (d, 2H), 6.98-7.05 (m, 2H), 6.90 (d, 2H), 3.65 (m, 4H), 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-cb609f09850342eb8294145516afdc70
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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