Cinnamoyl Chloride → methyl [4-({(4-dec-1-ynylbenzyl)[(2E)-3-phenylprop-2-enoyl]amino}methyl)phenoxy]acetate
Reaction equation
[C:1]([C:11]1[CH:31]=[CH:30][C:14]([CH2:15][NH:16][CH2:17][C:18]2[CH:29]=[CH:28][C:21]([O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:32]1(/[CH:38]=[CH:39]/[C:40](Cl)=[O:41])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[C:1]([C:11]1[CH:31]=[CH:30][C:14]([CH2:15][N:16]([CH2:17][C:18]2[CH:29]=[CH:28][C:21]([O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=2)[C:40](=[O:41])/[CH:39]=[CH:38]/[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]Participants
3
Procedure
The title compound was prepared following the procedure E using methyl (4-{[(4-dec-1-ynylbenzyl)amino]methyl}phenoxy)acetate and (2E)-3-phenylacryloyl chloride (purification by flash chromatography on SiO2-c-Hex/EtOAc 9:1) as a colorless oil (64%). M+ (ESI): 552.1. HPLC, Rt: 6.1 min (purity: 99.5%). 1H NMR (CDCl3) δ: 7.85 (m, 1H), 7.47-7.12 (m, 11H), 6.90 (m, 3H), 4.65-4.52 (m, 6H), 3.82 (s, 3H), 2.41 (t, J=7.0 Hz, 2H), 1.61 (m, 2H), 1.45 (m, 2H), 1.30 (m, 8H), 0.89 (t, J=6.8 Hz, 3H).
Sources & evidence
- ORD record
- ord-b0e533c94e584c1da6e3d0d7af6833a6
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589232B2
Reaction notes
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