Sodium Hydroxide → 4-{[{4-[(4-Butylphenyl)ethynyl]benzyl}(3-cyclopentylpropanoyl)amino]-methyl}benzoic acid
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]([CH2:28][C:29]3[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][CH:30]=3)[C:19](=[O:27])[CH2:20][CH2:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>>[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]([CH2:28][C:29]3[CH:38]=[CH:37][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=3)[C:19](=[O:27])[CH2:20][CH2:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
The titled compound was prepared following the procedure F using methyl 4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(3-cyclopentylpropanoyl)amino]methyl}benzoate and NaOH 1M as a yellow foam (77%). 1H NMR (CDCl3, 300 MHz) δ 8.15-8.02 (m, 2H), 7.56-7.40 (m, 4H), 7.33-7.22 (m, 2H), 7.21-7.08 (m, 4H), 4.69-4.58 (m, 2H), 4.54-4.43 (m, 2H), 2.61 (t, J=7.7 Hz, 2H), 2.49-2.35 (m, 2), 1.81-1.0 (m, 15H), 0.93 (t, J=7.3 Hz, 3H). M− (ESI): 520.4; M1(ESI): 522.3. HPLC, Rt: 5.71 min (Purity: 99.2%).
Sources & evidence
- ORD record
- ord-fa86c13454ed46a18fb6dfbcb1e66461
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589232B2
Reaction notes
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