Lithium Hydroxide → 4-{[(4-tert-butylphenyl)amino]carbonyl}benzoic Acid

HRID 1822929Notes

Reaction equation

HRID 1822929 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>O1CCCC1.CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:22][CH:23]=2)=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 7913868Methyl 4-{[(4-tert-butylphenyl)amino]carbonyl}benzoate

Product 1

HCID 141864734-{[(4-tert-butylphenyl)amino]carbonyl}benzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 23A (0.71 g, 2.28 mmol) in tetrahydrofuran (23 mL) and CH3OH (5.7 mL) was treated with 1N aqueous LiOH (5.7 mL, 5.7 mmol). After stirring overnight at room temperature, the organic solvents were removed under reduced pressure and the remaining aqueous solution was acidified to pH 1 with concentrated HCl. The acidified solution was extracted with ethyl acetate. The extracts were combined, dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.33 (s, 1H), 8.06 (m, 4H), 7.69 (m, 2H), 7.38 (m, 2H), 1.29 (s, 9H); MS (ESI+) m/z 298 (M+H)+.

Workup

  1. customthe organic solvents were removed under reduced pressure
  2. extractionThe acidified solution was extracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-23862680c8db4ea2ade1809f7ed588b0
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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