Lithium Hydroxide → 5-{[{4-[(4-Butylphenyl)ethynyl]benzyl}(hexyl)amino]carbonyl)-2-hydroxybenzoic acid

HRID 551920Notes

Reaction equation

HRID 551920 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:41]=[CH:40][C:16]([CH2:17][N:18]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:19]([C:21]3[CH:33]=[CH:32][C:24]4[O:25]C(C)(C)[O:27][C:28](=[O:29])[C:23]=4[CH:22]=3)=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Li+]>C1COCC1.O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:41]=[CH:40][C:16]([CH2:17][N:18]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:19]([C:21]3[CH:33]=[CH:32][C:24]([OH:25])=[C:23]([CH:22]=3)[C:28]([OH:29])=[O:27])=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11519643N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-hexyl-2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carboxamide

Product 1

HCID 575545135-{[{4-[(4-Butylphenyl)ethynyl]benzyl}(hexyl)amino]carbonyl)-2-hydroxybenzoic acidYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-hexyl-2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carboxamide (108 mg, 0.20 mmol) and lithium hydroxide (120 mg, 2.9 mmol) in THF (1 mL) and water (1 mL) was heated at 70° C. overnight. The solvents were removed under reduced pressure. The residue was taken up in EtOAc and washed with an aqueous solution of HCl (1N) and brine, dried over MgSO4 and the solvent was removed under reduced pressure to give 91 mg (91%) of hte title compound. HPLC, Rt: 5.72 min (purity: 98.9%).

Workup

  1. customThe solvents were removed under reduced pressure
  2. washwashed with an aqueous solution of HCl (1N) and brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-efb962f4683d480797f6665fafca0aaa
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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