3-Cyclopentylpropionyl chloride → Methyl 4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(3-cyclopentylpropanoyl)amino]methyl}benzoate
Reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:31]=[CH:30][C:16]([CH2:17][NH:18][CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH:32]1([CH2:37][CH2:38][C:39](Cl)=[O:40])[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][N:18]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[C:39](=[O:40])[CH2:38][CH2:37][CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:30][CH:31]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
The titled compound was prepared following the procedure E using methyl 4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]benzoate and 3-cyclopentylpropanoyl chloride as a colorless oil (71%). 1H NMR (CDCl3, 300 MHz) δ 8.02 (d, J=8.3 Hz, 1H), 7.97 (d, J=8.3 Hz, 1H), 7.54-7.39 (m, 4H), 7.30-7.06 (m, 6H), 4.61 (d, J=11.3 Hz, 2H), 4.48 (d, J=11.7 Hz, 2H), 3.91 (m, 3H), 2.61 (t, J=7.7 Hz, 2H), 2.41 (m, 2H), 1.79-1.66 (m, 4H), 1.65-1.43 (m, 7H), 1.40-1.28 (m, 2H), 1.14-1.00 (m, 2H), 0.92 (t, J=7.3 Hz, 3H). M+ (ESI): 536.4. HPLC, Rt: 6.42 min (Purity: 99%).
Sources & evidence
- ORD record
- ord-9fc7eefa599641978f2484d72d25189c
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589232B2
Reaction notes
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