Sodium Hydroxide → 4-[{4-[(4-Butylphenyl)ethynyl]benzyl}(3-cyclopentylpropanoyl)amino]-2-hydroxybenzoic acid
Reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:42]=[CH:41][C:16]([CH2:17][N:18]([C:28]3[CH:29]=[CH:30][C:31]4[C:36](=[O:37])[O:35]C(C)(C)[O:33][C:32]=4[CH:40]=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:42]=[CH:41][C:16]([CH2:17][N:18]([C:19](=[O:27])[CH2:20][CH2:21][CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)[C:28]3[CH:29]=[CH:30][C:31]([C:36]([OH:37])=[O:35])=[C:32]([OH:33])[CH:40]=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 C using N-{4-[(4-butylphenyl)ethynyl]benzyl}-3-cyclopentyl-N-(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-7-yl)propanamide and NaOH as a yellow powder (74%). 1H NMR (DMSO-d6, 300 MHz) δ 7.76 (d, J=8.3 Hz, 1H), 7.45 (m, 4H), 7.23 (m, 4H) 6.84 (m, 1H), 6.77 (m, 1H), 4.92 (s, 2H), 2.60 (t, J=7.6 Hz, 2H), 2.20 (t, J=7.3 Hz, 2H), 1.70-1.21 (m, 13H), 1.00-0.84 (m, 5H). HPLC, Rt: 5.84 min (Purity: 100%).
Sources & evidence
- ORD record
- ord-366d99df188041ce938ee2ab1614e548
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589232B2
Reaction notes
Loading…