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

HRID 733542Notes

Reaction equation

HRID 733542 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]([C:27]3[CH:39]=[CH:38][C:30]4[O:31]C(C)(C)[O:33][C:34](=[O:35])[C:29]=4[CH:28]=3)[C:19]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])=[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:41]=[CH:40][C:16]([CH2:17][N:18]([C:19]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])[C:27]3[CH:39]=[CH:38][C:30]([OH:31])=[C:29]([CH:28]=3)[C:34]([OH:35])=[O:33])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57841368N-{4-[(4-butylphenyl)ethynyl)benzyl}-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)cyclohexanecarboxamide

Product 1

HCID 117525695-[{4-[(4-Butylphenyl)ethynyl]benzyl)(cyclohexylcarbonyl)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)cyclohexanecarboxamide and NaOH (1N) in the presence of EtOH as a white powder (42%). 1H NMR (DMSO-d6, 300 MHz) δ 7.44 (m, 5H), 7.27-7.16 (m, 5H), 6.95 (d, J=8.7 Hz, 1H), 4.79 (s, 2H), 2.59 (t, J=7.8 Hz, 2H), 2.12 (m, 1H), 1.63-0.89 (m, 14H), 0.88 (t, J=7.4 Hz, 3H). M− (ESI): 508.3; M+ (ESI): 509.7. HPLC, Rt: 5.58 min (Purity: 99.8%).

Sources & evidence

ORD record
ord-7c1d688d1eb2408e93b66aaab148e0ba
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

Loading…