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

HRID 733544Notes

Reaction equation

HRID 733544 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:40]=[CH:39][C:16]([CH2:17][N:18]([C:26]3[CH:38]=[CH:37][C:29]4[O:30]C(C)(C)[O:32][C:33](=[O:34])[C:28]=4[CH:27]=3)[C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[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:40]=[CH:39][C:16]([CH2:17][N:18]([C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:26]3[CH:38]=[CH:37][C:29]([OH:30])=[C:28]([CH:27]=3)[C:33]([OH:34])=[O:32])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57841391N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)hexanamide

Product 1

HCID 160404775-[{4-[(4-Butylphenyl)ethynyl]benzyl}(hexanoyl)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)hexanamide and NaOH 5N aq in the presence of EtOH as a white foam (87%). 1R NMR (CDCl3, 300 MHz) δ 10.72 (s, 1H), 7.56 (d, J=2.5 Hz, 1H), 7.43 (m, 4H), 7.17 (m, 4H), 7.04 (dd, J=8.8, 2.5 Hz, 1H), 6.95 (d, J=8.8 Hz, 1H), 4.88 (s, 2H), 2.62 (t, J=7.7 Hz, 2H), 2.10 (t, J=7.6 Hz, 2H), 1.61 (m, 4H), 1.36 (m, 2H), 1.22 (m, 4H), 0.93 (t, J=7.3 Hz, 3H), 0.84 (t, J=6.7 Hz, 3H). M− (ESI): 496.4; M+ (ESI): 498.4. HPLC, Rt: 5.84 min (Purity: 100%).

Sources & evidence

ORD record
ord-19d846b296864620a29665f702eb7bfe
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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