Water → 3-[[2'-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyloxy]-4-nitrobenzoic acid morpholide

HRID 1939290Notes

Reaction equation

HRID 1939290 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:5]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)=[O:6].[H-].[Na+].[C:21]1([C:27]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:28]2[C:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[CH:44]=[CH:43][C:42]([CH2:45]Br)=[CH:41][CH:40]=3)=[N:31][N:30]=[N:29]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[C:53]1([C:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:28]2[C:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[CH:44]=[CH:43][C:42]([CH2:45][O:1][C:2]4[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=4[N+:16]([O-:18])=[O:17])[C:5]([N:7]4[CH2:12][CH2:11][O:10][CH2:9][CH2:8]4)=[O:6])=[CH:41][CH:40]=3)=[N:31][N:30]=[N:29]2)[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 120830123-Hydroxy-4-nitrobenzoic acid morpholide

Product 1

HCID 867517083-[[2'-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyloxy]-4-nitrobenzoic acid morpholideYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The compound ([3]-(32)-587) (0.99 g) prepared in Example 36 was dissolved in dry N,N-dimethylformamide (19 ml), and 50% sodium hydride (0.20 g) was added to the solution. The mixture was stirred at room temperature for 15 minutes. A solution of N-(triphenylmethyl)-5-[4'-(bromomethyl)biphenyl-2-yl]tetrazole (2.19 g) in N,N-dimethylformamide (6.5 ml) was added to the solution. The mixture was stirred at room temperature for 39 hours. The reaction mixture was added to water (50 ml), and extracted with chloroform (100 ml). The organic layer was washed, dried over anhydrous sodium sulfate, and concentrated to obtain the compound (2.72 g) as a light yellow solid. The product was purified by silica gel column chromatography (Kieselgel 60=190 g, chloroform/ethyl acetate=7/3) to obtain the compound ([3]-(33)-587) (1.41 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 39 hours
  2. extractionextracted with chloroform (100 ml)
  3. washThe organic layer was washed
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7dbd015dd9b94350a9c8c289a087c05d
Source dataset
uspto-grants-1997_12
Patent number
US05696118

Reaction notes

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