Potassium Hydroxide → 7-(3-(Phenyl)phenylcarbamoyl)heptanoic acid

HRID 1907716Notes

Reaction equation

HRID 1907716 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:19])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16])[CH:2]=1.[OH-].[K+]>C1COCC1>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:19])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:2]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59737409HCID 59737409, compound

Product 1

HCID 587568237-(3-(Phenyl)phenylcarbamoyl)heptanoic acidYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 182 (0.212 g, 0.62 mmol) in THF (10 mL) was treated with potassium hydroxide (5 mL of a 3.5% aqueous solution) and stirred at room temperature for 72 h then concentrated, diluted with diethyl ether and acidified with citric acid. The acidic mixture was extracted with AcOEt, washed with H2O, dried over MgSO4, filtered, and concentrated to give title compound 183 (0.182 g, 90% yield).

Workup

  1. concentrationthen concentrated
  2. additiondiluted with diethyl ether
  3. extractionThe acidic mixture was extracted with AcOEt
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-008b1acf031a421c820aa0e140e6c41c
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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