Sodium Hydroxide → 5-[{4-[(4-Butylphenyl)ethynyl]benzyl}(2,2-dimethylpropanoyl)amino]-2-hydroxybenzoic acid

HRID 733556Notes

Reaction equation

HRID 733556 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:39]=[CH:38][C:16]([CH2:17][N:18]([C:25]3[CH:37]=[CH:36][C:28]4[O:29]C(C)(C)[O:31][C:32](=[O:33])[C:27]=4[CH:26]=3)[C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CCO>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:39]=[CH:38][C:16]([CH2:17][N:18]([C:19](=[O:24])[C:20]([CH3:22])([CH3:21])[CH3:23])[C:25]3[CH:37]=[CH:36][C:28]([OH:29])=[C:27]([CH:26]=3)[C:32]([OH:33])=[O:31])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57841357N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)-2,2-dimethylpropionamide

Product 1

HCID 114545265-[{4-[(4-Butylphenyl)ethynyl]benzyl}(2,2-dimethylpropanoyl)amino]-2-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The titled compound was prepared following the procedure C using N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)-2,2-dimethylpropionamide and NaOH 5M aq. in the presence of EtOH as a white powder (70%). 1H NMR (CDCl3, 300 MHz) δ 10.62 (s, 1H), 7.55 (d, J=2.6 Hz, 1H), 7.43 (m, 4H), 7.15 (m, 4H), 7.08 (dd, J=8.7, 2.6 Hz, 1H), 6.93 (d, J=8.7 Hz, 1H), 4.83 (s, 2H), 2.62 (t, J=7.8 Hz, 2H), 1.61 (m, 2H), 1.36 (m, 2H, 1.08 (s, 9H), 0.93 (t, J=7.4 Hz, 3H). M− (ESI): 482.4; M+ (ESI): 484.3. HPLC, Rt: 5.39 min (Purity: 100%).

Sources & evidence

ORD record
ord-209d60f7d97f40dabd3d2214a676b753
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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