1-Octyne → ethyl[biS(4-oct-1-ynylbenzyl)amino](oxo)acetate
Reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([N:7]([CH2:23][C:24]1[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=1)=[O:6])[CH3:2].[CH:32]#[C:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>>[CH2:1]([O:3][C:4](=[O:31])[C:5]([N:7]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:32]#[C:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:26][CH:25]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][CH:10]=1)=[O:6])[CH3:2]Participants
3
Procedure
The same procedure as employed in the preparation of Example 226 (step c) but using ethyl[(4-bromobenzyl)(4-oct-1-ynylbenzyl)amino](oxo)acetate and 1-octyne gave the title compound as a pale yellow oil (32%). 1H NMR (CDCl3, 300 MHz) δ 7.38 (m, 4H), 7.16 (d, 2H, J=8.3 Hz), 7.12 (d, 2H, J=7.9 Hz), 4.45 (s, 2H), 4.35 (q, 2H, J=7.2 Hz), 4.28 (s, 2H), 2.42 (t, 4H, J=7.1 Hz), 1.62 (m, 4H), 1.47 (m, 4H), 1.33 (m, 11H), 0.92 (t, 6H, J=6.8 Hz). M+(LC/MS(ESI)): 514.0. HPLC (Condition A), Rt: 6.54 min (HPLC purity: 99.3%).
Workup
- customThe same procedure as employed in the preparation of Example 226 (step c)