Sodium Hydroxide → [4-({{4-[(4-Butylphenyl)ethynyl]benzyl}[(2-methoxyethoxy)acetyl]amino}methyl)phenoxy]acetic acid

HRID 733583Notes

Reaction equation

HRID 733583 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]([CH2:27][C:28]3[CH:39]=[CH:38][C:31]([O:32][CH2:33][C:34]([O:36]C)=[O:35])=[CH:30][CH:29]=3)[C:19](=[O:26])[CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.C1COCC1>[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]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([O:32][CH2:33][C:34]([OH:36])=[O:35])=[CH:38][CH:39]=3)[C:19](=[O:26])[CH2:20][O:21][CH2:22][CH2:23][O:24][CH3:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57841370Methyl [4-({{4-[(4-butylphenyl)ethynyl]benzyl}[(2-methoxyethoxy)acetyl]amino}methyl)phenoxy]acetate

Product 1

HCID 11466891[4-({{4-[(4-Butylphenyl)ethynyl]benzyl}[(2-methoxyethoxy)acetyl]amino}methyl)phenoxy]acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The titled compound was prepared following the procedure F using methyl [4-({{4-[(4-butylphenyl)ethynyl]benzyl}[(2-methoxyethoxy)acetyl]amino}methyl)phenoxy]acetate and NaOH 1N in the presence of MeOH/THF as a yellow oil (94%). 1H NMR (DMSO-d6, 300 MHz) δ 7.54-7.43 (m, 4H), 7.24 (m, 4H), 7.14 (d, J=8.3 Hz, 2H), 6.86 (m, 2H), 4.62 (s, 2H), 4.41 (m, 4H), 4.28 (s, 1H), 4.20 (s, 1H), 3.59 (m, 2H), 3.42 (m, 2H), 3.21 (s, 1.5H), 3.19 (s, 1.5H), 2.60 (t, J=7.5 Hz, 2H), 1.55 (m, 2H), 1.30 (m, 2H), 0.89 (t, J=7.2 Hz, 3H). M− (ESI): 542.4; M+ (ESI): 544.4. HPLC, Rt: 4.82 min (Purity: 90.8%).

Sources & evidence

ORD record
ord-a7140aadeeb54d76970a97c8bda841e3
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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