Sodium Hydroxide → 5-((4-tert-Butylbenzoyl){4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-hydroxybenzoic acid

HRID 733546Notes

Reaction equation

HRID 733546 reaction equation
[C:1]([C:5]1[CH:45]=[CH:44][C:8]([C:9]([N:11]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[C:33][C:34]3[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][CH2:42][CH3:43])=[CH:36][CH:35]=3)=[CH:28][CH:27]=2)[C:12]2[CH:24]=[CH:23][C:15]3[O:16]C(C)(C)[O:18][C:19](=[O:20])[C:14]=3[CH:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:11]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[C:33][C:34]3[CH:35]=[CH:36][C:37]([CH2:40][CH2:41][CH2:42][CH3:43])=[CH:38][CH:39]=3)=[CH:28][CH:27]=2)[C:12]2[CH:24]=[CH:23][C:15]([OH:16])=[C:14]([CH:13]=2)[C:19]([OH:20])=[O:18])=[O:10])=[CH:44][CH:45]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 578413254-tert-butyl-N-{4-[(4-butylphenyl)ethynyl]benzyl)-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)benzamide

Product 1

HCID 160406405-((4-tert-Butylbenzoyl){4-[(4-butylphenyl)ethynyl]benzyl}amino)-2-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The titled compound was prepared following the procedure C using 4-tert-butyl-N-{4-[(4-butylphenyl)ethynyl]benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)benzamide and NaOH 1M aq. in the presence of EtOH as a white powder (61%). 1H NMR (McOD, 300 MHz) δ 7.63 (d, J=2.3 Hz, 1H), 7.46 (d, J=8.3 Hz, 2H), 7.43 (d, J=8.3 Hz, 2H), 7.33 (m, 6H), 7.22 (d, J=8.3 Hz, 2H), 6.85 (brd, J=8.7 Hz, 1H), 6.62 (d, J=8.7 Hz, 1H), 5.13 (s, 2H), 2.66 (t, J=7.5 Hz, 2H), 1.64 (m, 2H), 1.41 (m, 2H), 1.26 (s, 9H), 0.97 (t, J=7.3 Hz, 3H). M− (ESI): 558.3. HPLC, Rt: 5.72 min (Purity: 97.9%).

Sources & evidence

ORD record
ord-bc1f8017676a486f9e8c6ca8ba58338b
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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