Sodium Hydroxide → 5-[{4-[(4-Butylphenyl)ethynyl]benzyl}(7-carboxyheptanoyl)amino]-2-hydroxybenzoic acid

HRID 733552Notes

Reaction equation

HRID 733552 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:45]=[CH:44][C:16]([CH2:17][N:18]([C:31]3[CH:43]=[CH:42][C:34]4[O:35]C(C)(C)[O:37][C:38](=[O:39])[C:33]=4[CH:32]=3)[C:19](=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])=[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:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:45]=[CH:44][C:16]([CH2:17][N:18]([C:19](=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:31]3[CH:43]=[CH:42][C:34]([OH:35])=[C:33]([CH:32]=3)[C:38]([OH:39])=[O:37])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57841326methyl 8-[{4-[(4-butylphenyl)ethynyl]benzyl}(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]-8-oxooctanoate

Product 1

HCID 113419125-[{4-[(4-Butylphenyl)ethynyl]benzyl}(7-carboxyheptanoyl)amino]-2-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The titled compound was prepared following the procedure C using methyl 8-[{4-[(4-butylphenyl)ethynyl]benzyl}(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-6-yl)amino]-8-oxooctanoate and NaOH 1M aq in the presence of EtOH as a white powder (35%). 1H NMR (CDCl3, 300 MHz) δ 10.69 (br s, 1H), 7.57 (d, J=2.3 Hz, 1H), 7.43 (m, 4H), 7.16 (m, 4H), 7.02 (dd, J=8.7, 2.3 Hz, 1H), 6.94 (d, J=8.7 Hz, 1H), 4.87 (s, 2H), 2.62 (t. J=7.5 Hz, 2H), 2.30 (t, J=7.4 Hz, 2H), 2.11 (t, J=7.3 Hz, 2H), 1.60 (m, 6H), 1.36 (m, 2H), 1.25 (m, 4H), 0.93 (t, J=7.3 Hz, 3H). M− (ESI): 554.3, M+ (ESI): 556.4. HPLC, Rt: 5.03 min (Purity: 99%).

Sources & evidence

ORD record
ord-e6907a9dacb048059746ae71325555aa
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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