Reaction equation
[CH2:1]([N:5]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]#[N:32])=[CH:21][CH:20]=1)[C:6](=[O:17])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([OH:16])=[O:15])[CH2:2][CH2:3][CH3:4].C([Sn]([N:46]=[N+:47]=[N-:48])(CCCC)CCCC)CCC.[OH-].[Na+].C(Cl)Cl.CO>C1(C)C(C)=CC=CC=1>[CH2:1]([N:5]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[NH:48][N:47]=[N:46][N:32]=2)=[CH:23][CH:24]=1)[C:6](=[O:17])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([OH:16])=[O:15])[CH2:2][CH2:3][CH3:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2.50 g of 2-carboxy-phenylacetic acid N-butyl-N-(2'-cyanobiphenyl-4-ylmethyl)-amide and 6.50 g of tributyltin azide in 50 ml of xylene is heated under reflux for 15 hours. When cool, the mixture is stirred with 50 ml of 2N sodium hydroxide solution at room temperature for 30 minutes. The aqueous phase is acidified and extracted three times with 50 ml of CH2C2 each time. After customary treatment, the combined dichloromethane phases yield a crude product that, after chromatography on silica gel 60 (40-63 μm) using CH2Cl2 /CH3OH (97:3)) as eluant, yields 2-carboxy-phenylacetic acid N-butyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amide that has an Rf value of 0.37 [CH2Cl2 /CH3OH (4:1)]. ##STR11##
Workup
- temperatureunder reflux for 15 hours
- temperatureWhen cool
- extractionextracted three times with 50 ml of CH2C2 each time
- customAfter customary treatment, the combined dichloromethane phases yield a crude product that
Sources & evidence
- ORD record
- ord-f5648ef2d9994a0ba933532ae6e55815
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05369110
Linked notes
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