Hexanoyl chloride → Methyl (4-{[(4-dec-1-ynylbenzyl) (hexanoyl)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](Cl)(=[O:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>>[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:32](=[O:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[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 G using methyl (4-{[(4-dec-1-ynylbenzyl)amino]methyl}phenoxy)acetate and hexanoyl chloride (purification by flash chromatography on SiO2, c-Hex/EtOAc 9:1) as a colorless oil (63%). M+ (ESI): 520.6. HPLC, Rt: 6.2 min (purity: 99.30%). 1H NMR (CDCl3) δ: 7.39 (d, J=8.3 Hz, 1H), 7.34 (d, J=7.9 Hz, 1H), 7.16-7.05 (m, 4H), 6.91 (d, J=8.7 Hz. 1H), 6.85 (d, J=8.7 Hz, 1H), 4.65 (s, 1H), 4.63 (s, 1H), 4.54 (s, 1H), 4.52 (s, 1H), 4.40 (s, 1H), 4.36 (s, 1H), 3.83 (s, 1.5H), 3.82 (s, 1.5H), 2.41 (m, 4H), 1.70 (m, 2H), 1.61 (m, 2H), 1.45 (m, 2H), 1.31 (brs, 12H), 0.90 (m, 6H).
Sources & evidence
- ORD record
- ord-0eedbfa54c294197ba4df74491ffed14
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589232B2
Reaction notes
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