Reaction equation
[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28]([C:29]([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:7](=[O:10])[NH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].Br[CH:49]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:50]([O:52][CH3:53])=[O:51]>>[CH2:1]([C:5]1[N:6]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:28]([C:29]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[N:27]=[N:26][N:25]=3)=[CH:16][CH:17]=2)[C:7](=[O:10])[N:8]([CH:49]([C:50]([O:52][CH3:53])=[O:51])[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[N:9]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Reactant 2
Product 1
Procedure
The alkylation of 5-n-butyl-2,4-dihydro-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one (from Example 2, Step D) with methyl α-bromophenyl-acetate was carried out as described in Example 3, Step A, except 3 equivalents of the alkylating agent was used. After work-up, flash chromatography of the crude product over silica gel (50 mL for 0.24 mmole, elution with 0.5% MeOH/CH2Cl2) gave the title compound in 57% yield as an oil, homogeneous by TLC in 2% MeOH/CH2Cl2, mass spectrum (FAB) m/e 766 (M+1)+.
Sources & evidence
- ORD record
- ord-498e6b5eba2c43d4a957517d7cb0c428
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05411980
Linked notes
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